Thiazolidine → (S)-N-{2-[2-Amino-3-oxo-3-(1,3-thiazolidin-3-yl)propylthio]-ethyl}-methanesulphonamide hydrochloride

HRID 2083968Notes

Reaction equation

C(OC([NH:11][CH2:12][CH2:13][S:14][CH2:15][C@H:16]([C:25]([OH:27])=O)[NH:17]C(OC(C)(C)C)=O)=O)C1C=CC=CC=1.[CH3:28][S:29]([Cl:32])(=[O:31])=[O:30].[S:33]1[CH2:37][CH2:36][NH:35][CH2:34]1>>[ClH:32].[NH2:17][C@@H:16]([C:25](=[O:27])[N:35]1[CH2:36][CH2:37][S:33][CH2:34]1)[CH2:15][S:14][CH2:13][CH2:12][NH:11][S:29]([CH3:28])(=[O:31])=[O:30]

Participants

Reactant 3

HCID 10444Thiazolidine

HCID 31297Methanesulfonyl chloride

HCID 11409801(S)-3-(2-{[benzyloxycarbonyl]-amino}-ethylthio)-N-(tert-butyloxy-carbonyl)-alanine

Product 1

HCID 69891997(S)-N-{2-[2-Amino-3-oxo-3-(1,3-thiazolidin-3-yl)propylthio]-ethyl}-methanesulphonamide hydrochloride

Procedure

Starting from (S)-3-(2-{[benzyloxycarbonyl]-amino}-ethylthio)-N-(tert-butyloxy-carbonyl)-alanine, methanesulphonyl chloride and 1,3-thiazolidine, the expected product is obtained according to the procedure described in Example 37.

Sources & evidence

ORD record: ord-efa9d10bedac44deaf25d2cb35396961
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716843B2

Reaction notes

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