HCID 131714247, compound → HCID 13531538, compound

HRID 1248499Notes

Reaction equation

HRID 1248499 reaction equation
[C:1]([O:9][C@@H:10]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:11](=[O:32])[CH2:12][C@@H:13]([CH3:31])[C:14]([N:16]1[CH2:30][CH2:29][CH2:28][C@H:17]1[C:18]([O:20]CC1C=CC=CC=1)=[O:19])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[C:1]([O:9][C@@H:10]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:11](=[O:32])[CH2:12][C@@H:13]([CH3:31])[C:14]([N:16]1[CH2:30][CH2:29][CH2:28][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 131714247HCID 131714247, compound

Product 1

HCID 13531538HCID 13531538, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[(5S,2R)-5-(benzoyloxy)-2-methyl-1,4-dioxo-6-phenylhexyl]-L-proline, phenylmethyl ester (230 mg., 0.435 mmole) and 10% palladium on carbon catalyst (50 mg.) in ethyl acetate (15 ml.) is stirred under hydrogen gas for 4 hours. The resulting mixture is filtered (millipore) and the filtrate concentrated to give the desired product as a colorless solid which is then dried under vacuum over P2O5 to give 144 mg. of 1-[(5S,2R)-5-(benzoyloxy)-2-methyl-1,4-dioxo-6-phenylhexyl]-L-proline; m.p. 130°-134°; [α]D20 =-110° (c=1.09, pyridine); Rf =0.37 [silica gel, ethyl acetate:pyridine:acetic acid; water (180:20:6:11)].

Workup

  1. filtrationThe resulting mixture is filtered (millipore)
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-bad49c24eff6491bb886597283096f5a
Source dataset
uspto-grants-1985_06
Patent number
US04524212

Reaction notes

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