Pyridine → tert-Butyl 1-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}-benzyl)cyclopropanecarboxylate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C.N1C=CC=CC=1.[NH2:32][C:33]1[CH:34]=[C:35]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:36][C:37]1([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:39][CH2:38]1>ClCCl>[Cl:50][C:49]1[CH:48]=[CH:47][C:35]([CH2:36][C:37]2([C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[CH2:39][CH2:38]2)=[CH:34][C:33]=1[NH:32][C:9](=[O:11])[C@H:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@@H:12]([CH3:17])[C:13]([F:16])([F:15])[F:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
368 mg (1.38 mmol) of (2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid were dissolved in 15 ml of dichloromethane, 246 mg (1.84 mmol) of 1-chloro-N,N,2-trimethylprop-1-en-1-amine were added and the mixture was then stirred at room temperature for 30 min. 279 μl (3.45 mmol) of pyridine and 324 mg (1.15 mmol) of tert-butyl 1-(3-amino-4-chlorobenzyl)-cyclopropanecarboxylate were then added, and the reaction mixture was stirred at room temperature for another 1 h. The reaction mixture was then concentrated under reduced pressure and the crude product obtained was purified by preparative RP-HPLC (mobile phase acetonitrile/water). This gave 540 mg of the target compound (88% of theory).
Workup
- stirringthe reaction mixture was stirred at room temperature for another 1 h
- concentrationThe reaction mixture was then concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-00fe9cba5886497787e10b953e2b4161
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018258B2
Reaction notes
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