BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID

Base Information

• Chemical Name: BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID
• CAS No.: 117918-23-7
• Molecular Formula: C11H19 N O4 S
• Molecular Weight: 261.342
• Hs Code.: 29349990
• Mol file: 117918-23-7.mol

Synonyms:3,4-Thiazolidinedicarboxylicacid, 5,5-dimethyl-, 3-(1,1-dimethylethyl) ester, (R)-;(4R)-5,5-Dimethylthiazolidine-3,4-dicarboxylic acid 3-tert-butyl ester;(R)-3-tert-Butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

Chemical Property of BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID

Chemical Property:

• PSA: 92.14000
• LogP: 2.09750
• Storage Temp.: Store at 0-5°C

Purity/Quality:

98%Min ^*data from raw suppliers

Boc-(r)-5,5-dimethylthiazolidine-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID

There total 7 articles about BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC 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: 66.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + 5,5-dimethylthiazolidine-4-carboxylic acid (72778-00-8) → (tert-butyloxycarbonyl)-L-5,5-dimethylthiazolidine-4-carboxylic acid (117918-23-7)

Guidance literature:

With triethylamine; In water; acetone;

DOI:10.1021/jm00122a030

Reference yield: 42.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (72778-00-8) → (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (117918-23-7)

Guidance literature:

With sodium hydroxide; In isopropyl alcohol;

DOI:10.1016/S0960-894X(03)00262-2

Reference yield: 23.6%

methyl (+/-)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate (85929-61-9) + di-tert-butyl dicarbonate (24424-99-5) → (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (117918-23-7)

Guidance literature:

methyl (+/-)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate; With Klebsiella oxytoca hydrolase; In water; at 60 ℃; for 26h;

With sodium hydroxide; pH=11.5;

di-tert-butyl dicarbonate; In sodium hydroxide; isopropyl alcohol; at 20 ℃; for 4h;

DOI:10.1016/S0957-4166(02)00257-4

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

5,5-dimethylthiazolidine-4-carboxylic acid

L-penicillamine

di-tert-butyl dicarbonate

Downstream raw materials:

(R)-N-(2-methylbenzyl)-3-[(2S,3S)-2-hydroxy-3-[3-hydroxy-2-methylbenzoyl]amino-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

acetic acid 3-{(1S,2S)-1-benzyl-3-[(4R)-5,5-dimethyl-4-(2-methyl-benzylcarbamoyl)-thiazolidin-3-yl]-2-hydroxy-3-oxo-propylcarbamoyl}-2-methyl-phenyl ester

Acetic acid 3-{(1S,2S)-1-benzyl-3-[(R)-4-(2-chloro-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-2-hydroxy-3-oxo-propylcarbamoyl}-2-methyl-phenyl ester

Acetic acid 3-{(1S,2S)-1-benzyl-3-[(R)-5,5-dimethyl-4-(2-trifluoromethyl-benzylcarbamoyl)-thiazolidin-3-yl]-2-hydroxy-3-oxo-propylcarbamoyl}-2-methyl-phenyl ester

Refernces

• 1、 Lu, Zhijian,Raghavan, Subharekha,Bohn, Joann,Charest, Mark,Stahlhut, Mark W.,Rutkowski, Carrie A.,Simcoe, Amy L.,Olsen, David B.,Schleif, William A.,Carella, Anthony,Gabryelski, Lori,Jin, Lixia,Lin, Jiunn H.,Emini, Emilio,Chapman, Kevin,Tata, James R.. "Design and synthesis of highly potent HIV protease inhibitors with activity against resistant virus". . p. 1821 - 1824. Retrieved 2007/10/03.
• 2、 Mimoto, Tsutomu,Kato, Ryohei,Takaku, Haruo,Nojima, Satoshi,Terashima, Keisuke,Misawa, Satoru,Fukazawa, Tominaga,Ueno, Takamasa,Sato, Hideharu,Shintani, Makoto,Kiso, Yoshiaki,Hayashi, Hideya. "Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine". . p. 1789 - 1802. Retrieved 2007/10/03.