(+/-)-tert-Butyl 1-[3-({cyclopentyl[4-(2,2-difluorovinyl)phenyl]acetyl}amino)benzyl]cyclopropanecarboxylate → (+/-)-tert-Butyl 1-[3-({cyclopentyl[4-(2,2-difluoroethyl)phenyl]acetyl}amino)benzyl]cyclopropanecarboxylate
Reaction equation
[CH:1]1([CH:6]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[C:34]([F:36])[F:35])=[CH:29][CH:28]=2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=2)[CH2:13][C:14]2([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([CH:6]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH:34]([F:35])[F:36])=[CH:29][CH:28]=2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=2)[CH2:13][C:14]2([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:16][CH2:15]2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
100 mg of Pd/C (10%) were added to a solution of 200.0 mg (0.404 mmol) of (+/−)-tert-butyl 1-[3-({cyclopentyl[4-(2,2-difluorovinyl)phenyl]acetyl}amino)benzyl]cyclopropanecarboxylate in 5 ml of ethanol. Under atmospheric pressure, the mixture was stirred vigorously under an atmosphere of hydrogen overnight. The reaction was then filtered off through Celite and the filtrate was concentrated under reduced pressure. The crude product was purified by preparative RP-HPLC (mobile phase acetonitrile/water). This gave 151.1 mg (75.2% of theory) of the target compound.
Workup
- filtrationThe reaction was then filtered off through Celite
- concentrationthe filtrate was concentrated under reduced pressure
- customThe crude product was purified by preparative RP-HPLC (mobile phase acetonitrile/water)
Sources & evidence
- ORD record
- ord-cecdabd261e44ef5ae341d1939050c08
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018258B2
Reaction notes
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