(S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester → (S)-Thiazolidine-2-carboxylic acid [4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-yl]-amide

HRID 737185Notes

Reaction equation

HRID 737185 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][S:10][C@H:9]1[C:13](=[O:32])[NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:31])[NH:27][CH:28]3[CH2:30][CH2:29]3)=[CH:22][CH:21]=2)[N:19]=1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH:28]1([NH:27][C:26]([C:23]2[CH:22]=[CH:21][C:20]([C:18]3[N:19]=[C:15]([NH:14][C:13]([C@H:9]4[NH:8][CH2:12][CH2:11][S:10]4)=[O:32])[S:16][CH:17]=3)=[CH:25][CH:24]=2)=[O:31])[CH2:30][CH2:29]1

Participants

4

Reactant 1

HCID 57849787(S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 86616434(S)-Thiazolidine-2-carboxylic acid [4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-yl]-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (S)-2-[4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester (341.6 mg, 0.72 mmol) in dichloromethane (3 mL) and trifluoroacetic acid (3 mL) was stirred at ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product.

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-4c5de14eb8514bbfb6e839cc74ede4a5
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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