N2 [3(S)-[[N-[4-(benzyloxycarbonyl)benzoyl]-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-L-prolinamide → HCID 86746240, compound

HRID 1757734Notes

Reaction equation

HRID 1757734 reaction equation
[N:1]#[N:2].C([O:10][C:11]([C:13]1[CH:52]=[CH:51][C:16]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@@H:28]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@H:29]([OH:43])[CH2:30][C@@:31]2([C:40]([NH2:42])=[O:41])[CH2:35][CH2:34][CH2:33][N:32]2[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:26])[CH2:21][C:22](=[O:24])[NH2:23])=[O:18])=[CH:15][CH:14]=1)=[O:12])C1C=CC=CC=1>C(O)(C)C.[Pd]>[N:1]#[N:2].[C:11]([C:13]1[CH:52]=[CH:51][C:16]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@@H:28]([CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@H:29]([OH:43])[CH2:30][C@@:31]2([C:40]([NH2:42])=[O:41])[CH2:35][CH2:34][CH2:33][N:32]2[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:26])[CH2:21][C:22](=[O:24])[NH2:23])=[O:18])=[CH:15][CH:14]=1)([OH:12])=[O:10]

Participants

4

Reactant 1

HCID 86746242N2 [3(S)-[[N-[4-(benzyloxycarbonyl)benzoyl]-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert.butyl-L-prolinamide

Product 1

HCID 86746240HCID 86746240, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

274 mg of N2 -[3(S)-[[N-[4-(benzyloxycarbonyl)-benzoyl]-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide in 100 ml of isopropanol were hydrogenated over 10% palladium-on-carbon at 20° C. and under atmospheric pressure for 16 hours. The catalyst was removed by filtration and the filtrate was evaporated to give 193 mg of N2 -[3(S)-[[N-(4-carboxybenzoyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide as a white solid from methanol/ethylacetate: MS: m/e 596 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-38219999574347df8f40ec801a63856e
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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