Hydrochloric Acid → 5-[4-(4-(2-(4-Methylthio-2-aminobutyramido)-2-methoxycarbonylethyl)phenoxy) benzylidene]thiazolidin-2,4-dione Hydrochloride

HRID 7355Notes

Reaction equation

HRID 7355 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH:5]([NH:36]C(OC(C)(C)C)=O)[C:6]([NH:8][CH:9]([C:32]([O:34][CH3:35])=[O:33])[CH2:10][C:11]1[CH:31]=[CH:30][C:14]([O:15][C:16]2[CH:29]=[CH:28][C:19]([CH:20]=[C:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1)=[O:7].[ClH:44]>ClCCl>[ClH:44].[CH3:1][S:2][CH2:3][CH2:4][CH:5]([NH2:36])[C:6]([NH:8][CH:9]([C:32]([O:34][CH3:35])=[O:33])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH:20]=[C:21]3[S:25][C:24](=[O:26])[NH:23][C:22]3=[O:27])=[CH:28][CH:29]=2)=[CH:30][CH:31]=1)=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 865974465-[4-(4-(2-(4-Methylthio-2-t-butoxycarbonylaminobutyramido)-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione

Product 1

HCID 865974455-[4-(4-(2-(4-Methylthio-2-aminobutyramido)-2-methoxycarbonylethyl)phenoxy) benzylidene]thiazolidin-2,4-dione HydrochlorideYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-[4-(4-(2-(4-methylthio-2-t-butoxycarbonylaminobutyramido)-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione (1.38 g, 2.2 mmol) in dichloromethane (30 ml) was bubbled with HCl gas at −10° C. for 80 minutes. The excess HCl gas was removed by N2 bubbling and the solvent was removed by distillation to furnish the title compound (1 g, yield 80.6%).

Workup

  1. customThe excess HCl gas was removed by N2 bubbling
  2. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-25127b0bf1854ea0bc85f57270ceb0a7
Source dataset
uspto-grants-2006_08
Patent number
US07087576B2

Reaction notes

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