tert-Butyl ((3S,5S,6S,8S)-8-((3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-yl)carbamate

Base Information

• Chemical Name: tert-Butyl ((3S,5S,6S,8S)-8-((3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-yl)carbamate
• CAS No.: 173338-07-3
• Molecular Formula: C35H61N3O8
• Molecular Weight: 651.885
• European Community (EC) Number: 605-675-0
• UNII: S744PYU6D7
• DSSTox Substance ID: DTXSID90693581
• Nikkaji Number: J2.829.789K
• Wikidata: Q82622593
• Mol file: 173338-07-3.mol

Synonyms:173338-07-3;N-Boc Aliskiren;tert-Butyl ((3S,5S,6S,8S)-8-((3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-yl)carbamate;S744PYU6D7;UNII-S744PYU6D7;Tert-butyl N-[(3S,5S,6S,8S)-8-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-6-hydroxy-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-2,9-dimethyldecan-5-yl]carbamate;Carbamic acid, N-((1S,2S,4S)-4-(((3-amino-2,2-dimethyl-3-oxopropyl)amino)carbonyl)-2-hydroxy-1-((2S)-2-((4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutyl)-5-methylhexyl)-, 1,1-dimethylethyl ester;CarbaMic acid, [4-[[(3-aMino-2,2-diMethyl-3-oxopropyl)aMino]carbonyl]-2-hydroxy-1-[2-[[4-Methoxy-3-(3-Methoxypropoxy)phenyl]Methyl]-3-Methylbutyl]-5-Methylhexyl]-, 1,1-diMethylethyl ester, [1S-[1R*(R*),2R*,4R*]]-;tert-Butyl ((3S,5S,6S,8S)-8-((3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl)-6-hydrxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-yl)carbamate;SCHEMBL842334;DTXSID90693581;CS-0272006;EN300-7548394;((1S, 2S, 4S)-4-(2-carbamoyl-2-methyl-propylcarbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methylbutyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester;((1S,2S,4S)-4-(2-carbamoyl-2-methyl-propycarbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methylbutyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester;(2S,4S,5S,7S)-N-(3-Amino-2,2-dimethyl-3-oxopropyl)-2-isopropyl-4-hydroxy-5-[(tert-butyloxycarbonyl)amino]-7-[3-(3-methoxypropoxy)-4-methoxybenzyl]-8-methylnonanamide;[4-[[(3-amino-2,2-dimethyl-3-oxopropyl)amino]carbonyl]-2-hydroxy-1-[2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-5-methylhexyl]-,1,1-dimethylethyl ester,[1S-[1R(R),2R,4R]];tert-Butyl [(3S,5S,6S,8S)-8-[(3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl]-6-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-2,9-dimethyldecan-5-yl]carbamate;tert-butyl N-[(1S,3S,4S,6S)-1-[(2-carbamoyl-2,2-dimethylethyl)carbamoyl]-3-hydroxy-6-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-7-methyl-1-(propan-2-yl)octan-4-yl]carbamate

Chemical Property of tert-Butyl ((3S,5S,6S,8S)-8-((3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-yl)carbamate

Chemical Property:

• Vapor Pressure: 8.94E-28mmHg at 25°C
• Boiling Point: 810.7°C at 760 mmHg
• PKA: 12.02±0.46(Predicted)
• Flash Point: 444.1°C
• PSA: 158.44000
• Density: 1.071g/cm³
• LogP: 6.34160
• Storage Temp.: 2-8°C
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 22
• Exact Mass: 651.44586591
• Heavy Atom Count: 46
• Complexity: 920

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Boc-Aliskiren ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC1=CC(=C(C=C1)OC)OCCCOC)CC(C(CC(C(C)C)C(=O)NCC(C)(C)C(=O)N)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)[C@@H](CC1=CC(=C(C=C1)OC)OCCCOC)C[C@@H]([C@H](C[C@@H](C(C)C)C(=O)NCC(C)(C)C(=O)N)O)NC(=O)OC(C)(C)C

Technology Process of tert-Butyl ((3S,5S,6S,8S)-8-((3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-yl)carbamate

There total 91 articles about tert-Butyl ((3S,5S,6S,8S)-8-((3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate (866030-35-5) + aminopivalinamide (324763-51-1) → tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate (173338-07-3)

Guidance literature:

With 2-Ethylhexanoic acid; In n-heptane; at 60 ℃; Reagent/catalyst; Temperature; Solvent; Time;

Reference yield: 70.0%

(2R,3S,5S)-tert-butyl 5-((1S,3S)-3-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-1-hydroxy-4-methylpentyl)-3-isopropyl-2-(4-methoxy-3-(3-methoxypropoxy)phenyl)pyrrolidine-1-carboxylate (916793-76-5) → tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate (173338-07-3)

Guidance literature:

With ammonia; sodium; tert-butyl alcohol; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

DOI:10.1021/ol100427v

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate (173338-07-3)

Guidance literature:

Multi-step reaction with 15 steps

1: NaBH₄ / ethanol

2: PBr₃ / CH₂Cl₂

3: 76 percent / LiHMDS / tetrahydrofuran

4: 81 percent / LiOH; H₂O₂

5: 95 percent / LAH / tetrahydrofuran

6: 97 percent / PPh₃; NBS / CH₂Cl₂

7: 68 percent / n-BuLi

8: HCl / acetonitrile

9: Et₃N

10: NaBH₄ / ethanol

11: 89 percent / DMSO; ClC(O)C(O)Cl; Et₃N / CH₂Cl₂

12: Mg

13: 23 percent / H₂ / Pd(OH)2/C

14: 38 percent / TPAP; NMMO

15: 65 percent / 2-hydroxypyridine; Et₃N

With 2-hydroxypyridin; hydrogenchloride; lithium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; oxalyl dichloride; hydrogen; dihydrogen peroxide; phosphorus tribromide; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; 11: Swern oxidation;

DOI:10.1016/j.tetlet.2005.07.028

upstream raw materials:

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate

aminopivalinamide

(2-carbamoyl-2-methylpropyl)carbamic acid benzyl ester

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Downstream raw materials:

aliskiren

(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Refernces

• 1、 Rossi, Sergio,Benaglia, Maurizio,Porta, Riccardo,Cotarca, Livius,Maragni, Paolo,Verzini, Massimo. "A stereoselective catalytic nitroaldol reaction as the key step in a strategy for the synthesis of the renin inhibitor aliskiren". supporting information. p. 2531 - 2537. Retrieved 2015/04/22.
• 2、 -. "PROCESS FOR THE PREPARATION OF ALISKIREN". Paragraph 0078; 0079. . Retrieved 2014/09/29.