(S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester
• CAS No.: 333426-35-0
• Molecular Formula: C₂₀H₃₂N₂O₅S
• Molecular Weight: 412.55
• Mol file: 333426-35-0.mol

Synonyms:(S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester

Chemical Property of (S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester

There total 5 articles about (S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester 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: 82.0%

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + (R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyric acid (333426-31-6) → (S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester (333426-35-0)

Guidance literature:

(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyric acid; With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 1h;

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)02300-5

Reference yield:

(R)-(-)-N-(3-methylbutan-2-ylidene)-2-methylpropane-2-sulfinamide (220263-58-1) → (S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester (333426-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / diethyl ether; hexane / -10 - 20 °C

1.2: AlMe₃ / toluene; diethyl ether; hexane / 0 °C

2.1: 63 percent / NaIO₄ / RuCl₃*H₂O / CH₂Cl₂; acetonitrile; H₂O / 18 h

3.1: HATU; Et₃N / dimethylformamide / 1 h

3.2: 82 percent / dimethylformamide

With sodium periodate; n-butyllithium; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; ruthenium trichloride; In diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)02300-5

Reference yield:

2-Methyl-propane-2-sulfinic acid [(R)-1,2-dimethyl-1-(5-methyl-furan-2-yl)-propyl]-amide (333426-26-9) → (S)-2-[(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyrylamino]-3-phenyl-propionic acid methyl ester (333426-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 63 percent / NaIO₄ / RuCl₃*H₂O / CH₂Cl₂; acetonitrile; H₂O / 18 h

2.1: HATU; Et₃N / dimethylformamide / 1 h

2.2: 82 percent / dimethylformamide

With sodium periodate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; ruthenium trichloride; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)02300-5

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

(R)-2,3-Dimethyl-2-(2-methyl-propane-2-sulfonylamino)-butyric acid

(R)-(-)-N-(3-methylbutan-2-ylidene)-2-methylpropane-2-sulfinamide

2-Methyl-propane-2-sulfinic acid [(R)-1,2-dimethyl-1-(5-methyl-furan-2-yl)-propyl]-amide