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(1S,2S)-(1-Benzyl-3-chloro-2-hydroxypropyl)carbamic acid tert-butyl ester
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Name

(1S,2S)-(1-Benzyl-3-chloro-2-hydroxypropyl)carbamic acid tert-butyl ester

 EINECS 1312995-182-4
CAS No. 165727-45-7 Density 1.153 g/cm3
PSA 58.56000 LogP 3.11300
Solubility N/A Melting Point N/A
Formula C15H22ClNO3 Boiling Point 460.5 °C at 760 mmHg
Molecular Weight 299.798 Flash Point 232.3 °C
Transport Information N/A Appearance White to off-white powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 165727-45-7 ((1S, 2S)-(1-BENZYL-3-CHLORO-2-HYDROXY-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER) Hazard Symbols N/A
Synonyms

Carbamicacid, [(1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-, 1,1-dimethylethylester (9CI);Carbamic acid, [3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-,1,1-dimethylethyl ester, [S-(R*,R*)]-;(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane;(2S,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane;(2S,3S)-N-tert-Butoxycarbonyl-3-amino-1-chloro-2-hydroxy-4-phenylbutane;[(1S)-1-((1S)-2-Chloro-1-hydroxyethyl)-2-phenylethyl]carbamic acid tert-butylester;

Article Data 30

(1S,2S)-(1-Benzyl-3-chloro-2-hydroxypropyl)carbamic acid tert-butyl ester Synthetic route

102123-74-0

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
With isopropyl alcohol; aluminum tri-tert-butoxide In dichloromethane at 50℃; Product distribution / selectivity; Meerwein-Ponndorf-Verley Reduction; Inert atmosphere;95%
With aluminum sec-butoxide In 2-methyl-propan-1-ol; toluene at 15 - 20℃; Large scale;95%
With C38H40ClN2O3RhS In dichloromethane at 25℃; for 1h; Catalytic behavior; Schlenk technique; diastereoselective reaction;93%
102123-74-0

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

67-63-0

isopropyl alcohol

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene90%
102123-74-0

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

A

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

B

162536-40-5

(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane

C

(1R,2R)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester

D

923601-69-8

(1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With potassium phosphate buffer; Streptomyces nodosus SC 13149 at 28℃; for 48h; pH=6.8; microbial reduction;A 62%
B n/a
C n/a
D n/a
102123-74-0

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

A

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

B

162536-40-5

(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 0.75h;A 50%
B n/a
With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 0.75h;A n/a
B 50%
With sodium tetrahydroborate In ethanol; toluene at -78 - 0℃; for 8h;A 7.8 g
B n/a

potassium bisulfite

102123-74-0

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
With sodium borohydrid In tetrahydrofuran; water; ethyl acetate50%
24424-99-5

di-tert-butyl dicarbonate

(S)-3-amino-(S)-2-hydroxy-4-phenyl-1-chlorobutane hydrochloride

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine
With triethylamine In tetrahydrofuran at 20℃; Cooling with ice;
51987-73-6

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LDA / tetrahydrofuran / 0.5 h / -78 °C
2: 7.8 g / NaBH4 / toluene; ethanol / 8 h / -78 - 0 °C
View Scheme
7535-56-0

N-t-butoxycarbonyl-L-phenylalanine 4-nitrophenyl ester

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: t-BuOK / tetrahydrofuran / 2 h / Heating
1.2: tetrahydrofuran / 4 h / 0 °C
2.1: 81 percent / LiCl; MeSO3H / tetrahydrofuran / 2 h / 70 °C
3.1: 50 percent / NaBH4 / tetrahydrofuran; H2O / 0.75 h / 0 °C
View Scheme
400611-25-8

tert-butyl (S)-(4-(dimethyl(oxo)-λ6-sulfanylidene)-3-oxo-1-phenylbutan-2-yl)carbamate

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / LiCl; MeSO3H / tetrahydrofuran / 2 h / 70 °C
2: 50 percent / NaBH4 / tetrahydrofuran; H2O / 0.75 h / 0 °C
View Scheme
123054-12-6, 123808-74-2, 136370-73-5, 111060-64-1

(2S)-N,N-dibenzylphenylalaninal

165727-45-7

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Li / tetrahydrofuran / -55 °C
2: 97 percent / H2 / Pd(OH)2/C / 760 Torr
3: Et3N
View Scheme
Multi-step reaction with 3 steps
1: lithium / tetrahydrofuran / 3 h / -65 °C / Inert atmosphere
2: palladium hydroxide on carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr
3: triethylamine / tetrahydrofuran / 20 °C / Cooling with ice
View Scheme

(1S,2S)-(1-Benzyl-3-chloro-2-hydroxypropyl)carbamic acid tert-butyl ester Specification

The (1S,2S)-(1-Benzyl-3-chloro-2-hydroxypropyl)carbamic acid tert-butyl ester is a kind of organic compounds with cas registry number of 165727-45-7. It has a systematic name which is called tert-butyl [(1S,2S)-1-benzyl-3-chloro-2-hydroxypropyl]carbamate.

The physical properties about this chemical are: (1)ACD/LogP: 3.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.38; (4)ACD/LogD (pH 7.4): 3.38; (5)ACD/BCF (pH 5.5): 218.91; (6)ACD/BCF (pH 7.4): 218.9; (7)ACD/KOC (pH 5.5): 1647.29; (8)ACD/KOC (pH 7.4): 1647.22; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.527; (13)Molar Refractivity: 79.86 cm3; (14)Molar Volume: 259.7 cm3; (15)Surface Tension: 41.6 dyne/cm; (16)Density: 1.153 g/cm3; (17)Flash Point: 232.3 °C; (18)Enthalpy of Vaporization: 75.98 kJ/mol; (19)Boiling Point: 460.5 °C at 760 mmHg; (20)Vapour Pressure: 2.83E-09 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: ClC[C@@H](O)[C@@H](NC(=O)OC(C)(C)C)Cc1ccccc1;
(2)InChI: InChI=1/C15H22ClNO3/c1-15(2,3)20-14(19)17-12(13(18)10-16)9-11-7-5-4-6-8-11/h4-8,12-13,18H,9-10H2,1-3H3,(H,17,19)/t12-,13+/m0/s1;
(3)InChIKey: GFGQSTIUFXHAJS-QWHCGFSZBV

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