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

HRID 7352Notes

Reaction equation

HRID 7352 reaction equation
C(OC([NH:8][CH:9]([CH3:40])[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:41]>ClCCl>[ClH:41].[NH2:8][CH:9]([CH3:40])[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 219896705-[4-(4-(2-(2-t-Butoxycarbonylaminopropanamido}2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione

Product 1

HCID 219896635-[4-(4-(2-(2-Aminopropanamido)-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione HydrochlorideYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-[4-(4-(2-(2-t-butoxycarbonylaminopropanamido}2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione (1 g, 1.75 mmol) in dichloromethane (10 ml) was bubbled with HCl gas at −10° C. for 50 minutes. The excess HCl gas was removed by N2 bubbling and concentrated to dryness to afford the title compound (0.59 g, yield 66.3%).

Workup

  1. customThe excess HCl gas was removed by N2 bubbling
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9c8ede02f9314b8780028afe08414a5a
Source dataset
uspto-grants-2006_08
Patent number
US07087576B2

Reaction notes

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