Ethanol → HCID 13146121, compound

HRID 1980259Notes

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].C([CH:20]([S:26][CH:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH3:28])[C:21](=O)[C:22]([O-:24])=[O:23])C.C([BH3-])#N.[Na+].[CH2:38](O)[CH3:39]>>[CH2:32]([O:31][C:29]([CH:27]([S:26][CH2:20][CH:21]([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:22]([O:24][CH2:38][CH3:39])=[O:23])[CH3:28])=[O:30])[CH3:33]

Participants

Reactant 4

HCID 702Ethanol2×

HCID 5003444Sodium cyanoborohydride

HCID 13146116HCID 13146116, compound

HCID 20232331HCID 20232331, compound

Product 1

HCID 13146121HCID 13146121, compound

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-9cf0c02403ca4b52b4faedbd2cb2aa78
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04508729

Reaction notes

Loading…