Diisopropylcarbodiimide → 4-(2-(ethyldisulfanyl)-6-methylphenyl) 1-(2-phenylpropan-2-yl) (S)-2-((tert-butoxycarbonyl)amino)succinate
Reaction equation
[CH2:1]([S:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12])[CH3:2].C(N=C=NC(C)C)(C)C.[C:22]([O:26][C:27]([NH:29][C@H:30]([C:35](=[O:46])[O:36][C:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([CH3:39])[CH3:38])[CH2:31][C:32](O)=[O:33])=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C)C1C=CN=CC=1.ClCCl>[C:22]([O:26][C:27]([NH:29][C@@H:30]([CH2:31][C:32]([O:12][C:6]1[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:5]=1[S:4][S:3][CH2:1][CH3:2])=[O:33])[C:35]([O:36][C:37]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([CH3:39])[CH3:38])=[O:46])=[O:28])([CH3:25])([CH3:23])[CH3:24]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
2-(Ethyldisulfanyl)-6-methylphenol (Compound 105) (423 mg, 2.11 mmol), N,N′-diisopropylcarbodiimide (0.329 ml, 2.11 mmol) and N,N-dimethylpyridin-4-amine (34.4 mg, 0.282 mmol) were added to a solution of (S)-3-((tert-butoxycarbonyl)amino)-4-oxo-4-((2-phenylpropan-2-yl)oxy)butanoic acid (Compound 109) (495 mg, 1.41 mmol) in dichloromethane (7 ml), and the mixture was stirred at room temperature for 1 hour. The reaction solution was then purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→0/100) to afford 4-(2-(ethyldisulfanyl)-6-methylphenyl) 1-(2-phenylpropan-2-yl) (S)-2-((tert-butoxycarbonyl)amino)succinate (Compound 110) (249 mg, 33%).
Workup
- customThe reaction solution was then purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→0/100)
Sources & evidence
- ORD record
- ord-8cfede431c8b4131be0e5f7d5d7685be
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
Loading…