Acetic Acid → Rac-cis-2-[4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]cyclopentanecarboxylic acid

HRID 737213Notes

Reaction equation

HRID 737213 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@@H:6]1[C:10](=[O:29])[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:28])[NH:24][CH:25]3[CH2:27][CH2:26]3)=[CH:19][CH:18]=2)[N:16]=1)=[O:4].[Li+].[OH-].CC(O)=O>C1COCC1.CO.O>[CH:25]1([NH:24][C:23]([C:20]2[CH:21]=[CH:22][C:17]([C:15]3[N:16]=[C:12]([NH:11][C:10]([C@H:6]4[CH2:7][CH2:8][CH2:9][C@H:5]4[C:3]([OH:4])=[O:2])=[O:29])[S:13][CH:14]=3)=[CH:18][CH:19]=2)=[O:28])[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 87485281Rac-cis-2-[4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 87483907Rac-cis-2-[4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]cyclopentanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Rac-cis-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-cyclopentanecarboxylic acid methyl ester (100 mg) was dissolved in THF:MeOH:H2O (2:2:1, 5 mL) and treated with LiOH (10 eq. 45 mg) and stirred at room temperature for 15 hours. The mixture was neutralized with HOAc, and the solvents removed. The resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. MS: 400.5 (M+H+)

Workup

  1. customthe solvents removed
  2. dissolutionThe resulting mixture was redissolved in 5 ml of 90% DMF
  3. custom10% water with 0.1% TFA and purified by reverse phase HPLC
  4. customto give the product

Sources & evidence

ORD record
ord-3c1794223b014549b60562344a96d614
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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