HCID 13531534, compound → HCID 70489780, compound

HRID 1248497Notes

Reaction equation

HRID 1248497 reaction equation
[C:1]([O:9][C@@H:10]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:11](=[O:24])[CH2:12][CH2:13][C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[CH2:1]([O:9][C@@H:10]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:11](=[O:24])[CH2:12][CH2:13][C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 13531534HCID 13531534, compound

Product 1

HCID 70489780HCID 70489780, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[(5S)-5-(benzoyloxy)-1,4-dioxo-6-phenylhexyl]-L-proline (250 mg., 0.5 mmole), 10% palladium on carbon catalyst (50 mg.), and ethyl acetate (10 ml.) is stirred under hydrogen gas for 7.5 hours. The solution is filtered (millipore), and the solvent removed at reducted pressure. Ether is added to the residue and crystals form. The solution is filtered to give the desired product as a white hygroscopic solid which is dried under vacuum over P2O5 to give 150 mg. of 1-[(5S)-5-(benzoyloxy)-1,4-dioxo-6-phenylhexyl]-L-proline; Rf =0.40 [silica gel, ethyl acetate:pyridine:acetic acid:water (100:20:6:11)]; m.p. 114°-115°;

Workup

  1. filtrationThe solution is filtered (millipore)
  2. customthe solvent removed at reducted pressure
  3. additionEther is added to the residue and crystals form
  4. filtrationThe solution is filtered

Sources & evidence

ORD record
ord-3ec136a26fb6452684c75632e1b0d6c8
Source dataset
uspto-grants-1985_06
Patent number
US04524212

Reaction notes

Loading…