Ethyl alpha-oxobenzenebutanoate → HCID 22827204, compound

HRID 1463026Notes

Reaction equation

HRID 1463026 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][C@@H:12]([CH2:14][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]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24].C([BH3-])#N.[Na+]>C(O)C>[CH2:26]([O:25][C:23]([C@@H:22]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][C@@H:12]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])[CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 22827195HCID 22827195, compound

Product 1

HCID 22827204HCID 22827204, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(L-alanyl)-4-(S)-(phenylmethyl)-L-proline and ethyl 2-oxo-4-phenylbutyrate in ethanol is stored at room temperature with powdered molecular sieves. Over the course of several hours, sodium cyanoborohydride is added and the reaction mixture is filtered and concentrated under reduced pressure. The residue is purified by absorption on ion exchange resin to yield 1-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylmethyl)-L-proline.

Workup

  1. customis stored at room temperature with powdered molecular sieves
  2. filtrationthe reaction mixture is filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by absorption on ion exchange resin

Sources & evidence

ORD record
ord-d4eead9512b04e3282a59bb47899979e
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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