Hydrochloric Acid → 5-[4-(4-(2-Amino-2-methoxycarbonylethyl) phenoxy)benzilidene]thiazolidin-2,4-dione

HRID 1007285Notes

Reaction equation

HRID 1007285 reaction equation
C(OC([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)(C)(C)C.Cl>C(Cl)Cl>[NH2:8][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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 765731105-[4-(4-(2-t-Butoxycarbonylamino-2-methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dione

Product 1

HCID 730387895-[4-(4-(2-Amino-2-methoxycarbonylethyl) phenoxy)benzilidene]thiazolidin-2,4-dioneYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-[4-(4-(2-t-butoxycarbonylamino-2-methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dione (2 g, 4.0 mmol) in DCM (100 ml) at 0° C. was bubbled with HCl gas. After stirring for 1 hour, the yellow precipitate was filtered and 1.7 g (3.9 mmol) of HCl-Tyr (C6H4-CH=TDZ)-OMe was collected with 97.5% yield, mp: 187-190° C. The HPLC purity of product was 94.5%. Compound 1.

Workup

  1. filtrationthe yellow precipitate was filtered
  2. custom1.7 g (3.9 mmol) of HCl-Tyr (C6H4-CH=TDZ)-OMe was collected with 97.5% yield, mp: 187-190° C

Sources & evidence

ORD record
ord-d280a7da900c482799724dc524e3468a
Source dataset
uspto-grants-2004_09
Patent number
US06794401B2

Reaction notes

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