Thiazolidine → (S)-N-[3-Amino4-oxo4-(1,3-thiazolidin-3-yl)butyl]-methane-sulphonamide hydrochloride

HRID 2083948Notes

Reaction equation

C(OC([NH:11][CH2:12][CH2:13][C@H:14]([NH:18]C(OC(C)(C)C)=O)[C:15]([OH:17])=O)=O)C1C=CC=CC=1.[CH3:26][S:27]([Cl:30])(=[O:29])=[O:28].[S:31]1[CH2:35][CH2:34][NH:33][CH2:32]1>>[ClH:30].[NH2:18][C@H:14]([C:15](=[O:17])[N:33]1[CH2:34][CH2:35][S:31][CH2:32]1)[CH2:13][CH2:12][NH:11][S:27]([CH3:26])(=[O:29])=[O:28]

Participants

Reactant 3

HCID 10444Thiazolidine

HCID 31297Methanesulfonyl chloride

HCID 7019688(S)-4-(((Benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)butanoic acid

Product 1

HCID 69890633(S)-N-[3-Amino4-oxo4-(1,3-thiazolidin-3-yl)butyl]-methane-sulphonamide hydrochloride

Procedure

Starting from (S)-4-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)-amino]-butanoic acid, methanesulphonyl chloride and 1,3-thiazolidine, the expected product is obtained according to the procedure described in Example 3.

Sources & evidence

ORD record: ord-900f138d61ac4a0aa258a36a4a8ba372
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716843B2

Reaction notes

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