Sodium cyanoborohydride → HCID 13146121, compound

HRID 1285142Notes

Reaction equation

HRID 1285142 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

HCID 5003444Sodium cyanoborohydrideHCID 13146116HCID 13146116, compoundHCID 13146117HCID 13146117, compound

Product 1

HCID 13146121HCID 13146121, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1 g (4.17 m mols) 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' stirring at room temperature, 0.25 g of sodium cyanoborohydride in solution in 2.25 ml of anhydrous ethanol are added within 6 hours.

Sources & evidence

ORD record
ord-5bc3560f1e76472990a1b5e47d710e63
Source dataset
uspto-grants-1986_01
Patent number
US04565819

Reaction notes

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