Diisopropylcarbodiimide → (S)-benzyl 2-((tert-butoxycarbonyl)amino)-5-oxo-5-((4-(trifluoromethyl)phenyl)thio)pentanoate
Reaction equation
C(N=C=NC(C)C)(C)C.[F:10][C:11]([F:20])([F:19])[C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.[CH2:21]([O:28][C:29](=[O:44])[C@@H:30]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:31][CH2:32][C:33](O)=[O:34])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[C:40]([O:39][C:37]([NH:36][C@@H:30]([CH2:31][CH2:32][C:33](=[O:34])[S:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([F:10])([F:19])[F:20])=[CH:17][CH:16]=1)[C:29]([O:28][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:44])=[O:38])([CH3:43])([CH3:42])[CH3:41]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
N,N′-Diisopropylcarbodiimide (0.510 ml, 3.26 mmol), N,N-dimethylaminopyridine (45.2 mg, 0.370 mmol), 4-(trifluoromethyl)benzenethiol (0.211 ml, 1.55 mmol) were added to a solution of (S)-5-(benzyloxy)-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid (Compound 5a-2) (500 mg, 1.48 mmol) in dichloromethane (5 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was then purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→20/80) to afford (S)-benzyl 2-((tert-butoxycarbonyl)amino)-5-oxo-5-((4-(trifluoromethyl)phenyl)thio)pentanoate (Compound 5f-2) (373 mg, 51%).
Workup
- customThe reaction mixture was then purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→20/80)
Sources & evidence
- ORD record
- ord-d9c30e009ce24571b689934af5b203d3
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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