Diisopropylcarbodiimide → (S)-benzyl 2-((tert-butoxycarbonyl)amino)-5-((4-fluorophenyl)thio)-5-oxopentanoate
Reaction equation
C(N=C=NC(C)C)(C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1.[CH2:18]([O:25][C:26](=[O:41])[C@@H:27]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:28][CH2:29][C:30](O)=[O:31])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[C:37]([O:36][C:34]([NH:33][C@@H:27]([CH2:28][CH2:29][C:30]([S:17][C:14]1[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=1)=[O:31])[C:26]([O:25][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:41])=[O:35])([CH3:40])([CH3:39])[CH3:38]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-fluorobenzenethiol (0.164 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-((4-fluorophenyl)thio)-5-oxopentanoate (Compound 5e-2) (540 mg, 82%).
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-19dec51a93d54994add0eea8dcd3a7b4
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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