Thiazolidine → (S)-N-[5-Amino-6-oxo-(1,3-thiazolidin-3-yl)-hexyl]-N-methyl-methanesulphonamide hydrochloride

HRID 2083976Notes

Reaction equation

C(O[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:25]([OH:27])=O)[NH:17]C(OC(C)(C)C)=O)=O)C1C=CC=CC=1.[N+](C1C=CC=C[C:32]=1[S:37]([Cl:40])(=[O:39])=[O:38])([O-])=O.[S:41]1[CH2:45][CH2:44][NH:43][CH2:42]1>>[ClH:40].[NH2:17][C@H:16]([C:25]([N:43]1[CH2:44][CH2:45][S:41][CH2:42]1)=[O:27])[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:9])[S:37]([CH3:32])(=[O:38])=[O:39]

Participants

Reactant 3

HCID 10444Thiazolidine

HCID 155402-Nitrobenzenesulfonyl chloride

HCID 2724765Boc-Lys(Z)-OH

Product 1

HCID 69890982(S)-N-[5-Amino-6-oxo-(1,3-thiazolidin-3-yl)-hexyl]-N-methyl-methanesulphonamide hydrochloride

Procedure

Starting from (S)-N6-(benzyloxycarbonyl)-N2-(tert-butyloxycarbonyl)-lysine, 2-nitrobenzenesulphonyl chloride and 1,3-thiazolidine, the expected product is obtained according to the procedure described in Steps A to C of Example 3.

Sources & evidence

ORD record: ord-f7d97a3fa7034acd8e43003c8e1aa590
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716843B2

Reaction notes

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