Sodium cyanoborohydride → 1-[N-(1-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline

HRID 1463023Notes

Reaction equation

HRID 1463023 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][C@@H:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].O=[C:22]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C([BH3-])#N.[Na+]>C(O)C>[CH2:26]([O:25][C:23]([CH:22]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][C@@H:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:24])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 18370473Benzyl 2-oxo-4-phenylbutanoateHCID 228271961-(L-alanyl)-4-(S)-(phenylthio)-L-proline

Product 1

HCID 228272001-[N-(1-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 200 mg. of 1-(L-alanyl)-4-(S)-(phenylthio)-L-proline and 1.1 grams of benzyl 2-oxo-4-phenylbutyrate in 8 ml. of ethanol is stored at room temperature with 3 grams of powdered molecular sieves (type 4A). Over the course of three hours, 75 mg. of sodium cyanoborohydride is added. The reaction mixture is filtered and concentrated under reduced pressure. The residue is purified by absorption on a strong cation exchange resin and elution with 2% pyridine in water. After passage through a gel filtration column, the desired product, 1-[N-(1-benzyloxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline, is obtained as a mixture of isomers that can be separated by high performance liquid chromatography.

Workup

  1. customOver the course of three hours, 75 mg
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by absorption on a strong cation exchange resin and elution with 2% pyridine in water
  5. filtrationAfter passage through a gel filtration column

Sources & evidence

ORD record
ord-a15ab7189b69413a991b13aa19ad5748
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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