Benzyloxycarbonyl-asparagine → HCID 70043568, compound

HRID 54069Notes

Reaction equation

HRID 54069 reaction equation
[C:1]([O:5][C:6](=[O:35])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13]([OH:34])[C@@H:14]([NH:23][C:24](OCC1C=CC=CC=1)=[O:25])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:36]([O:43][C:44]([NH:46][C@H:47](C(O)=O)[CH2:48][C:49](=[O:51])[NH2:50])=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:35])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13]([OH:34])[C@@H:14]([NH:23][C:24](=[O:25])[C@H:47]([CH2:48][C:49](=[O:51])[NH2:50])[NH:46][C:44]([O:43][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:45])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 75314Benzyloxycarbonyl-asparagineHCID 70041590HCID 70041590, compound

Product 1

HCID 70043568HCID 70043568, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 270 mg of N-[3(S)-(benzyloxyformamido)-4-(4-fluorophenyl)-2(R)-hydroxybutyl]-L-proline tert.butyl ester in 50 ml of ethanol was hydrogenated over 30 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 158 mg of N-(benzyloxycarbonyl)-L-asparagine in a manner analogous to that described in Example 1. The crude product was chromatographed on silica gel using 10% methanol in dichloromethane for the elution. There were obtained 120 mg of N-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-4-(4-fluorophenyl)-2(R)-hydroxybutyl]-L-proline tert.butyl ester as a white solid of melting point 163°-164° C.

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 silica gel using 10% methanol in dichloromethane for the elution

Sources & evidence

ORD record
ord-0070f00a2d234709ba2737afd4b6258a
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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