Hydrochloric Acid → 5-[4-(4-(2-(2-Aminoacetamido)-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione Hydrochloride

HRID 7354Notes

Reaction equation

HRID 7354 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][CH:13]([C:36]([O:38][CH3:39])=[O:37])[CH2:14][C:15]1[CH:35]=[CH:34][C:18]([O:19][C:20]2[CH:33]=[CH:32][C:23]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1)=[O:11])=O)(C)(C)C.[ClH:40]>ClCCl>[ClH:40].[NH2:8][CH2:9][C:10]([NH:12][CH:13]([C:36]([O:38][CH3:39])=[O:37])[CH2:14][C:15]1[CH:35]=[CH:34][C:18]([O:19][C:20]2[CH:33]=[CH:32][C:23]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219896645-[4-(4-(2-(2-t-Butoxycarbonylaminoacetamido)-2-methoxycarbonylethyl) phenoxy)benzyl]thiazolidin-2,4-dione

Product 1

HCID 219896525-[4-(4-(2-(2-Aminoacetamido)-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione HydrochlorideYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-[4-(4-(2-(2-t-butoxycarbonylaminoacetamido)-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione (0.73 g, 1.31 mmol) in dichloromethane (30 ml) was bubbled with HCl gas at −10° C. for 1.25 h. The excess HCl gas was removed by N2 bubbling and the solvent was removed by distillation to provide the title compound (0.51 g, yield 78.8%).

Workup

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

Sources & evidence

ORD record
ord-9e01c3eb0ed740a29320f8d952f36727
Source dataset
uspto-grants-2006_08
Patent number
US07087576B2

Reaction notes

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