Benzyloxycarbonyl-asparagine → N-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-(4-methoxyphenyl)butyl]-L-proline tert.butyl ester

HRID 54070Notes

Reaction equation

HRID 54070 reaction equation
[C:1]([O:5][C:6](=[O:36])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13]([OH:35])[C@@H:14]([NH:24][C:25](OCC1C=CC=CC=1)=[O:26])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:37]([O:44][C:45]([NH:47][C@H:48](C(O)=O)[CH2:49][C:50](=[O:52])[NH2:51])=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:36])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13]([OH:35])[C@@H:14]([NH:24][C:25](=[O:26])[C@H:48]([CH2:49][C:50](=[O:52])[NH2:51])[NH:47][C:45]([O:44][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:46])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 75314Benzyloxycarbonyl-asparagineHCID 70042910HCID 70042910, compound

Product 1

HCID 70041113N-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-(4-methoxyphenyl)butyl]-L-proline tert.butyl esterYield 10.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 730 mg of N-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-(4-methoxyphenyl)butyl]-L-proline tert.butyl ester in 20 ml of ethanol was hydrogenated over 50 mg of 10% palladium-on-carbon for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated to give an oil which was coupled with 340 mg of N-(benzyloxycarbonyl)-L-asparagine in a manner analogous to that described in Example 1. The crude product was chromatographed on a column of silica gel using 10% methanol in dichloromethane for the elution. There were obtained 82 mg of N-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-(4-methoxyphenyl)butyl]-L-proline tert.butyl ester as a white solid; MS: m/e 613 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customto give an oil which
  4. customThe crude product was chromatographed on a column of silica gel using 10% methanol in dichloromethane for the elution

Sources & evidence

ORD record
ord-1a43096cef7549f49aec8eea038369b2
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

Loading…