Citric Acid → HCID 178460517, compound
Reaction equation
C[Si](C)(C)[O-].[K+].[Cl:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]([C:17]2[O:18][C:19]([NH:22][C:23]3[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=3[F:31])=[N:20][N:21]=2)=[O:16])[CH:11]=[CH:10][C:9]=1[C@H:32]1[CH2:37][CH2:36][C@H:35]([CH:38]([CH3:44])[C:39]([O:41]CC)=[O:40])[CH2:34][CH2:33]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Cl:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]([C:17]2[O:18][C:19]([NH:22][C:23]3[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=3[F:31])=[N:20][N:21]=2)=[O:16])[CH:11]=[CH:10][C:9]=1[C@H:32]1[CH2:33][CH2:34][C@H:35]([CH:38]([CH3:44])[C:39]([OH:41])=[O:40])[CH2:36][CH2:37]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Potassium trimethylsilanolate (1.29 g, 9.98 mmol) was added in one portion to a stirred solution of rac-ethyl 2-(trans-4-{2-chloro-4-[({5-[(2,4,5-trifluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)propanoate (Example 641, 550 mg, 1.0 mmol) in THF (10 mL) and the reaction mixture was heated in the microwave at 90° C. for 20 min. The reaction mixture was concentrated in vacuo to leave a yellow solid and then a 1M aqueous solution of citric acid (40 mL) was added and the mixture was stirred for 30 mins. The mixture was filtered to leave a solid, which was washed with H2O (20 mL) to give the title compound (570 mg, 97%) as an off-white solid. The individual isomers may be separated by chiral chromatography under standard conditions and recrystallised from EtOH/water to give
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- customto leave a yellow solid
- filtrationThe mixture was filtered
- customto leave a solid, which
- washwas washed with H2O (20 mL)
Sources & evidence
- ORD record
- ord-1d0afd789bee4f01a2588a64bb67a6e8
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795283B2
Reaction notes
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