L-(+)-Cysteine → HCID 11398048, compound

HRID 1611641Notes

Reaction equation

HRID 1611641 reaction equation
[CH3:1][C:2]([NH:4][C@H:5]([C:8]([NH:10][CH2:11][CH2:12][S:13][C:14]([CH3:16])=[O:15])=[O:9])[CH2:6][SH:7])=[O:3].N[C@H](C(O)=O)CS.C(N[C@H](C(O)=O)CS[C:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)C.Cl.C(SCCN)(=O)C>>[C:2]([NH:4][C@H:5]([C:8]([NH:10][CH2:11][CH2:12][S:13][C:14](=[O:15])[CH3:16])=[O:9])[CH2:6][S:7][C:31]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 4

HCID 5862L-(+)-CysteineHCID 484333Ethanethioic acid, S-(2-(((2R)-2-(acetylamino)-3-mercapto-1-oxopropyl)amino)ethyl)esterHCID 519453S-(2-Aminoethyl) ethanethioate--hydrogen chloride (1/1)HCID 7408363HCID 7408363, compound

Product 1

HCID 11398048HCID 11398048, compound

Procedure

The first process for the preparation of the compound I-152 (scheme 1) corresponds to the process for the preparation of the compound of general formula (I) described above and involves correctly protected L-cysteine. This preparation process is characterized in that it comprises the following stages (i) of coupling of N-acetyl-S-trityl-L-cysteine (7) with S-acetylcysteamine hydrochloride to provide the compound N-(N-acetyl-S-trityl-L-cysteinyl)-S-acetylcysteamine (8); then (ii) of S-detritylation reaction of the compound N-(N-acetyl-S-trityl-L-cysteinyl)-S-acetylcysteamine, in solution in methanol and chloroform, with a mixture of silver nitrate, pyridine and methanol to provide the corresponding silver sulfide (9); then (iii) of suspending said corresponding silver sulfide in chloroform; then (iv) of release of the free thiol in the presence of HCl or H2S.

Sources & evidence

ORD record
ord-914bb704b8244f6099f8a6436140ff77
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

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