4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)-

Base Information

• Chemical Name: 4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)-
• CAS No.: 112878-95-2
• Molecular Formula: C19H20N2O3S
• Molecular Weight: 356.445
• Mol file: 112878-95-2.mol

Synonyms:

Chemical Property of 4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)-

There total 12 articles about 4-Imidazolidinecarboxylic acid, 5-(mercaptomethyl)-2-oxo-1,3-bis(phenylmethyl)-, (4R,5R)- 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: 95.0%

(2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetamide (541508-59-2) → (4R,5R)-1,3-dibenzyl-5-(mercaptomethyl)imidazolidin-2-one-4-carboxylic acid (112878-95-2)

Guidance literature:

(2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetamide; In N,N-dimethyl-formamide; at 90 ℃; for 1h;

With hydrogenchloride; Further stages.;

DOI:10.1016/j.tetlet.2004.07.034

Reference yield:

(4S,4'S,5R,5'R)-5,5'-[dithiobis-(methylene)]bis(1,3-dibenzyl-2-oxoimidazolidin-4-carboxamide) (541508-63-8) → (4R,5R)-1,3-dibenzyl-5-(mercaptomethyl)imidazolidin-2-one-4-carboxylic acid (112878-95-2)

Guidance literature:

(4S,4'S,5R,5'R)-5,5'-[dithiobis-(methylene)]bis(1,3-dibenzyl-2-oxoimidazolidin-4-carboxamide); With acetic acid; zinc; In water; at 55 - 60 ℃; for 1h;

With hydrogenchloride; In water; at 20 - 90 ℃; for 2h;

Reference yield:

(4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxamide (541508-64-9) → (4R,5R)-1,3-dibenzyl-5-(mercaptomethyl)imidazolidin-2-one-4-carboxylic acid (112878-95-2)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; at 90 ℃; for 3h;

DOI:10.1016/j.tetlet.2003.09.202

upstream raw materials:

(4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxamide

(2R)-2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetamide

2-[(4R)-3-benzyl-2-oxathiazolidin-4-yl]-2-benzylaminoacetonitrile

(R)-3-benzyl-2-oxothiazolidine-4-carbaldehyde

Downstream raw materials:

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

(4R,5R)-1,3-dibenzyl-3,3a,6,6a-tetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

biotin

5-[(3aR,6aS)-1,3-Dibenzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(6E)-ylidene]-pentanoic acid ethyl ester

Refernces

• 1、 Seki, Masahiko,Hatsuda, Masanori,Yoshida, Shin-Ichi. "An efficient and practical procedure for Strecker reaction: A highly diastereoselective synthesis of a key intermediate for (+)-biotin". . p. 6579 - 6581. Retrieved 2007/10/03.
• 2、 Seki, Masahiko,Kimura, Mayumi,Hatsuda, Masanori,Yoshida, Shin-Ichi,Shimizu, Toshiaki. "2-Thiazolidinone: A novel thiol protective surrogate of complete atom efficiency, a practical synthesis of (+)-biotin". . p. 8905 - 8907. Retrieved 2007/10/03.