Methanol → 4-(4-{3-[2-(3-Trifluoromethyl-benzoylamino)-acetylamino]-azetidin-1-yl}-cyclohexyl)-benzoic acid
Reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:19][CH:18]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[CH2:17]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.CO.O.O[Li].O>C1COCC1>[F:33][C:31]([F:32])([F:34])[C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[C:24]([NH:23][CH2:22][C:21]([NH:20][CH:18]1[CH2:17][N:16]([CH:13]2[CH2:14][CH2:15][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[CH2:19]1)=[O:36])=[O:35]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 4-(4-{3-[2-(3-trifluoromethyl-benzoylamino)-acetylamino]-azetidin-1-yl}-cyclohexyl)-benzoic acid methyl ester (less polar fraction from Example 9, 250 mg, 0.48 mmol) in THF (1 mL), MeOH (1 mL) and H2O (1 mL) was treated with LiOH.H2O (50 mg, 1.2 mmol) at room temperature. The reaction was then heated to 50° C. for 2 hours. The reaction was allowed to cool and solvent was removed in vacuo. 1 N HCl solution was added to adjust the solution to pH=6˜7. The white precipitate was collected by filtration and washed with water. The solid was dried in vacuo, re-dissolved in ethyl acetate and re-crystallization to afford the title compound.
Workup
- temperatureto cool
- customsolvent was removed in vacuo
- addition1 N HCl solution was added
- filtrationThe white precipitate was collected by filtration
- washwashed with water
- customThe solid was dried in vacuo
- dissolutionre-dissolved in ethyl acetate
- customre-crystallization
Sources & evidence
- ORD record
- ord-601aa89eeda942daa2f2f9a6041df4da
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513229B2
Reaction notes
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