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Formoterol
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Name

Formoterol

 EINECS N/A
CAS No. 73573-87-2 Density 1.233 g/cm3
PSA 90.82000 LogP 3.32310
Solubility DMSO: 20 mg/mL, soluble in water Melting Point N/A
Formula C19H24N2O4 Boiling Point 603.2 °C at 760 mmHg
Molecular Weight 344.411 Flash Point 318.6 °C
Transport Information N/A Appearance off-white solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 73573-87-2 (N-[2-Hydroxy-5-[1-hydroxy-2-[1-(4-methoxyphenyl)propan-2-ylamino]ethyl]phenyl]formamide) Hazard Symbols N/A
Synonyms

Eformoterol;Formamide,N-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-,(R*,R*)-;Formatris Novolizer;Oxis;

Article Data 13

Formoterol Synthetic route

188690-83-7

N-[5-[(1R)-Hydroxy-2-[[(1R)-methyl-2-(4-methoxyphenyl)ethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-formamide

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In ethanol at 25 - 30℃; under 2942.29 Torr; for 3h;80%
With hydrogen; palladium on activated charcoal In ethanol
With hydrogen; palladium 10% on activated carbon In methanol
With palladium 10% on activated carbon; hydrogen In isopropyl alcohol at 35 - 36℃; Autoclave;
408497-91-6

N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
With hydrogen; 10% palladium on active carbon In ethanol at 20℃; Hydrogenolysis;
64-13-1

2-amino-1-(4-methyoxyphenyl)propane

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Candida antarctica lipase B
2: 3M aq. KOH / Heating
3: dimethylsulfoxide / 87 h / 80 °C
4: neutral Al2O3 (activity III)
5: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
6: 69 percent / pyridine / 6.5 h / 60 °C
7: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
37629-51-9

1-methoxy-4-((E)-2-nitroprop-1-enyl)benzene

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 78 percent / LiAlH4 / diethyl ether / 2 h / Heating
2: Candida antarctica lipase B
3: 3M aq. KOH / Heating
4: dimethylsulfoxide / 87 h / 80 °C
5: neutral Al2O3 (activity III)
6: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
7: 69 percent / pyridine / 6.5 h / 60 °C
8: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: LiAlH4 / diethyl ether / 2 h / Heating
1.2: Candida antarctica lipase B; ethyl acetate; Et3N / 4 h / 30 °C
2.1: dimethylsulfoxide / 87 h / 80 °C
3.1: neutral Al2O3 (activity III)
4.1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
5.1: 69 percent / pyridine / 6.5 h / 60 °C
6.1: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
14347-05-8

4-benzyloxy-3-nitroacetophenone

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 82 percent / Br2 / CHCl3 / 25 °C
2: 87 percent / BH3*THF / tetrahydrofuran / -20 °C
3: lipase PS Celite-immobilized / various solvent(s) / 72 h / 37 °C
4: K2CO3 / methanol / 2.5 h / 20 °C
5: dimethylsulfoxide / 87 h / 80 °C
6: neutral Al2O3 (activity III)
7: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
8: 69 percent / pyridine / 6.5 h / 60 °C
9: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: 82 percent / Br2 / CHCl3 / 25 °C
2.1: BH3*THF / tetrahydrofuran / -20 °C
2.2: 48 percent / lipase PS; vinyl acetate / various solvent(s) / 72 h / 37 °C
3.1: K2CO3 / methanol / 2.5 h / 20 °C
4.1: dimethylsulfoxide / 87 h / 80 °C
5.1: neutral Al2O3 (activity III)
6.1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
7.1: 69 percent / pyridine / 6.5 h / 60 °C
8.1: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
43229-01-2

4-benzyloxy-3-nitrophenacyl bromide

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 87 percent / BH3*THF / tetrahydrofuran / -20 °C
2: lipase PS Celite-immobilized / various solvent(s) / 72 h / 37 °C
3: K2CO3 / methanol / 2.5 h / 20 °C
4: dimethylsulfoxide / 87 h / 80 °C
5: neutral Al2O3 (activity III)
6: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
7: 69 percent / pyridine / 6.5 h / 60 °C
8: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: BH3*THF / tetrahydrofuran / -20 °C
1.2: 48 percent / lipase PS; vinyl acetate / various solvent(s) / 72 h / 37 °C
2.1: K2CO3 / methanol / 2.5 h / 20 °C
3.1: dimethylsulfoxide / 87 h / 80 °C
4.1: neutral Al2O3 (activity III)
5.1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
6.1: 69 percent / pyridine / 6.5 h / 60 °C
7.1: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: 98 percent / oxazaborolidine from cis (1R,2S)-aminoindanol and trimethylboroxine, BH3 / tetrahydrofuran / -15 °C
2: 98 percent / aqueous sodium hydroxide / methanol / 0.5 h
3: 90 °C
4: H2 / PtO2
6: H2 / Pd-C / ethanol
View Scheme
58993-79-6

(R)-(-)-p-methoxyamphetamine

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dimethylsulfoxide / 87 h / 80 °C
2: neutral Al2O3 (activity III)
3: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
4: 69 percent / pyridine / 6.5 h / 60 °C
5: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
123-11-5

4-methoxy-benzaldehyde

(E/Z)-crotylstannane(1-)*Et4N(1+)

(E/Z)-crotylstannane(1-)*Et4N(1+)

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 81 percent / ammonium acetate / 0.58 h / Heating
2: 78 percent / LiAlH4 / diethyl ether / 2 h / Heating
3: Candida antarctica lipase B
4: 3M aq. KOH / Heating
5: dimethylsulfoxide / 87 h / 80 °C
6: neutral Al2O3 (activity III)
7: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
8: 69 percent / pyridine / 6.5 h / 60 °C
9: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 81 percent / ammonium acetate / 0.58 h / Heating
2.1: LiAlH4 / diethyl ether / 2 h / Heating
2.2: Candida antarctica lipase B; ethyl acetate; Et3N / 4 h / 30 °C
3.1: dimethylsulfoxide / 87 h / 80 °C
4.1: neutral Al2O3 (activity III)
5.1: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
6.1: 69 percent / pyridine / 6.5 h / 60 °C
7.1: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
299964-35-5

(+/-)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: lipase PS Celite-immobilized / various solvent(s) / 72 h / 37 °C
2: K2CO3 / methanol / 2.5 h / 20 °C
3: dimethylsulfoxide / 87 h / 80 °C
4: neutral Al2O3 (activity III)
5: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
6: 69 percent / pyridine / 6.5 h / 60 °C
7: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
188730-94-1

(R)-1-(4-benzyloxy-3-nitrophenyl)oxirane

73573-87-2

(R,R)-formoterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dimethylsulfoxide / 87 h / 80 °C
2: neutral Al2O3 (activity III)
3: 67 percent / Fe turnings; 1M aq. HCl / methanol / 0.75 h / Heating
4: 69 percent / pyridine / 6.5 h / 60 °C
5: H2 / 10 percentPd/C / ethanol / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 90 °C
2: H2 / PtO2
4: H2 / Pd-C / ethanol
View Scheme
Multi-step reaction with 4 steps
1.1: 20 h / 140 °C / Inert atmosphere
2.1: hydrogen / Ni-Raney / isopropyl alcohol; toluene / 20 h / 40 °C / 13680.9 Torr
3.1: acetic anhydride / 2 h / 50 °C / Inert atmosphere
3.2: 1 h / 0 °C
3.3: 0.25 h / 0 °C
4.1: hydrogen / 5% Pd(II)/C(eggshell) / ethanol / 20 h / 40 °C / 7600.51 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: 10 h / 20 - 110 °C
2.1: water; sodium dithionite / di-isopropyl ether; acetone; methanol / 20 - 60 °C
2.2: 25 - 60 °C / pH 9 - 9.5
3.1: polyethylene glycol-400 / 20 - 65 °C
3.2: pH 7 - 7.5
4.1: hydrogen / palladium 10% on activated carbon / methanol
View Scheme

Formoterol Specification

The Formamide,N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-,rel-, with CAS registry number 73573-87-2, belongs to the following product category: (intermediates of formoterol ). It has the systematic name of N-{2-hydroxy-5-[(1R)-1-hydroxy-2-{[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl]phenyl}formamide. This chemical is a kind of off-white solid. And the chemical formula of this chemical is C19H24N2O4.

Physical properties of Formamide,N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-,rel-: (1)ACD/LogP: 1.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.4; (4)ACD/LogD (pH 7.4): -0.07; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 3.93; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 51.24 Å2; (13)Index of Refraction: 1.616; (14)Molar Refractivity: 97.63 cm3; (15)Molar Volume: 279.1 cm3; (16)Polarizability: 38.7×10-24cm3; (17)Surface Tension: 53.6 dyne/cm; (18)Density: 1.233 g/cm3; (19)Flash Point: 318.6 °C; (20)Enthalpy of Vaporization: 94.35 kJ/mol; (21)Boiling Point: 603.2 °C at 760 mmHg; (22)Vapour Pressure: 2.12E-15 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=CNc1cc(ccc1O)[C@@H](O)CN[C@H](C)Cc2ccc(OC)cc2
(2)InChI: InChI=1/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1
(3)InChIKey: BPZSYCZIITTYBL-YJYMSZOUBO
(4)Std. InChI: InChI=1S/C19H24N2O4/c1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1
(5)Std. InChIKey: BPZSYCZIITTYBL-YJYMSZOUSA-N

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