Sodium cyanoborohydride → HCID 13146121, compound
Reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][C@H:7]1[C:15]([OH:17])=[O:16])=[O:5])[CH3:3].[CH2:18]([O:20][C:21]([CH:23]([S:25][CH2:26][C:27](=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:24])=[O:22])[CH3:19].C([BH3-])#N.[Na+]>C(O)C>[CH2:18]([O:20][C:21]([CH:23]([S:25][CH2:26][CH:27]([NH:1][C@H:2]([C:4]([N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][C@H:7]1[C:15]([OH:17])=[O:16])=[O:5])[CH3:3])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:24])=[O:22])[CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1 g (4.17 m moles) of (2S)-1-[(S)-alanyl]-2-carboxyperhydroindole, prepared as described in Example 3, Step F, and 4.72 g (19 m mols) of ethyl [(1RS)-1-ethoxycarbonylethylthio]-pyruvate are dissolved in 50 ml of anhydrous ethanol in the presence of 15 g of molecular sieve 4 Å. After 45 minutes's stirring at room temperature, 0.25 g of sodium cyanoborohydride in solution in 2.25 ml of anhydrous ethanol are added within 6 hours.