(R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid

Base Information

• Chemical Name: (R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid
• CAS No.: 519020-76-9
• Molecular Formula: C₁₂H₁₄ClNO₄
• Molecular Weight: 271.7
• Mol file: 519020-76-9.mol

Synonyms:(R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid

Chemical Property of (R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid

There total 2 articles about (R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid 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: 84.0%

(R)-4-chloromethyl-4-methyl-5-oxo-2-phenyloxazolidine-3-carboxylic acid benzyl ester (519020-70-3) → (R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid (519020-76-9)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 6h;

Reference yield:

(2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one (135923-86-3,135923-87-4,143564-89-0) → (R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid (519020-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / DMPU; LHMDS / tetrahydrofuran / 1.5 h / -78 °C

2: 84 percent / LiOH; H₂O / tetrahydrofuran / 6 h / 20 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; water; lithium hexamethyldisilazane; In tetrahydrofuran;

Reference yield: 88.0%

L-threonine methyl ester hydrochloride (39994-75-7) + (R)-2-benzyloxycarbonylamino-3-chloro-2-methylpropionic acid (519020-76-9) → (R)-N-benzyloxycarbonyl-2-chloromethylalanine-L-threonine methyl ester (519020-77-0)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃; for 24h;

upstream raw materials:

(R)-4-chloromethyl-4-methyl-5-oxo-2-phenyloxazolidine-3-carboxylic acid benzyl ester

(2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one

Downstream raw materials:

(R)-N-benzyloxycarbonyl-2-chloromethylalanine-L-threonine methyl ester

(R)-2-(1-benzyloxycarbonylamino-2-chloro-1-methylethyl)-5-methyloxazole-4-carboxylic acid methyl ester

(R)-2-(2-benzyloxycarbonylamino-3-chloro-2-methylpropionylamino)-3-oxobutyric acid methyl ester