HCID 131714797, compound → HCID 13657310, compound

HRID 364056Notes

Reaction equation

HRID 364056 reaction equation
[C:1]([NH:9][C@@H:10]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:11]([OH:32])[CH2:12][N: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>[OH-].[OH-].[Pd+2].C(O)C.C(OCC)(=O)C>[C:1]([NH:9][C@@H:10]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH:11]([OH:32])[CH2:12][N: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 131714797HCID 131714797, compound

Product 1

HCID 13657310HCID 13657310, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of 1-[[[(3S)-3-(benzoylamino)-2-hydroxy-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester (isomer A) (790 mg., 149 mmole), palladium hydroxide on carbon catalyst (110 mg.) and ethanol: ethyl acetate (1:1, 20 ml.) is stirred under hydrogen gas (balloon) for one hour. The solution is filtered (millipore), and the solvent removed at reduced pressure to give the desired product as a colorless solid. Drying under vacuum over phosphorus pentoxide yields 569 mg. of 1-[[[(3S)-3-(benzoylamino)-2-hydroxy-4-phenylbutyl]methylamino]carbonyl]-L-proline (isomer A); m.p. 108°-117°; [α]D20 =-77.5° (c=1.4, methanol). TLC (silica gel; chloroform:methanol:acetic acid; 18:1:1) Rf =0.39, trace at Rf =0.58.

Workup

  1. filtrationThe solution is filtered (millipore)
  2. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-868b1b0787de4fc880c45f765f213105
Source dataset
uspto-grants-1986_08
Patent number
US04604402

Reaction notes

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