Acetic Acid → HCID 87484684, compound

HRID 737181Notes

Reaction equation

HRID 737181 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].CO.[Li+].[OH-].CC(O)=O>C1COCC1>[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

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 57849777HCID 57849777, compound

Product 1

HCID 87484684HCID 87484684, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Rac-trans-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-cyclopentanecarboxylic acid methyl ester (100 mg) was dissolved in THF:MeOH:H20 (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-3aeda170f72848fd9278b3a72b099eb6
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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