Ethyl alpha-oxobenzenebutanoate → 1-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline

HRID 1463028Notes

Reaction equation

HRID 1463028 reaction equation
O=[C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:16][C@H:17]([C:19]([N:21]1[CH2:28][C@@H:27]([S:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26][C@H:22]1[C:23]([OH:25])=[O:24])=[O:20])[CH3:18].C([BH3-])#N.[Na+]>C(O)C.O>[CH2:6]([O:5][C:3]([C@@H:2]([NH:16][C@H:17]([C:19]([N:21]1[CH2:28][C@@H:27]([S:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:26][C@H:22]1[C:23]([OH:25])=[O:24])=[O:20])[CH3:18])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 228271961-(L-alanyl)-4-(S)-(phenylthio)-L-proline

Product 1

HCID 141030771-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

Ethyl 2-oxo-4-phenylbutyrate (1.03 gram) and 1-(L-alanyl)-4-(S)-(phenylthio)-L-proline (0.19 gram) are dissolved in a 1:1 ethanol-water solvent. A solution of sodium cyanoborohydride (0.19 gram) in ethanol-water is added dropwise at room temperature over the course of two hours. When the reaction is completed, the product is absorbed in strong acid ion exchange resin and eluted with 2% pyridine water. The product rich cuts are freeze dried and the desired isomer is separated chromatographically to yield 1-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline.

Workup

  1. customthe product is absorbed in strong acid ion exchange resin
  2. washeluted with 2% pyridine water
  3. customdried
  4. customthe desired isomer is separated chromatographically

Sources & evidence

ORD record
ord-3544960dea724a1faa146f9160c6d6b3
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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