N2 [3(S)-[[N-[6-(benzyloxycarbonyl)-2-naphthoyl]-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert-butyl-L-prolinamide → N2 [3(S)-[[N-(6-carboxy-2-naphthoyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert-butyl-L-prolinamide

HRID 54077Notes

Reaction equation

HRID 54077 reaction equation
[N:1]#[N:2].C([O:10][C:11]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:23]([NH:25][C@H:26]([C:31]([NH:33][C@@H:34]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C@H:35]([OH:49])[CH2:36][C@@:37]1([C:46]([NH2:48])=[O:47])[CH2:41][CH2:40][CH2:39][N:38]1[C:42]([CH3:45])([CH3:44])[CH3:43])=[O:32])[CH2:27][C:28](=[O:30])[NH2:29])=[O:24])[CH:17]=[CH:16]2)=[O:12])C1C=CC=CC=1>C(O)(C)C.[Pd]>[N:1]#[N:2].[C:11]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:23]([NH:25][C@H:26]([C:31]([NH:33][C@@H:34]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C@H:35]([OH:49])[CH2:36][C@@:37]1([C:46]([NH2:48])=[O:47])[CH2:41][CH2:40][CH2:39][N:38]1[C:42]([CH3:43])([CH3:44])[CH3:45])=[O:32])[CH2:27][C:28](=[O:30])[NH2:29])=[O:24])[CH:17]=[CH:16]2)([OH:12])=[O:10]

Participants

4

Reactant 1

HCID 86746238N2 [3(S)-[[N-[6-(benzyloxycarbonyl)-2-naphthoyl]-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert-butyl-L-prolinamide

Product 1

HCID 86746236N2 [3(S)-[[N-(6-carboxy-2-naphthoyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-tert-butyl-L-prolinamideYield 55.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

294 mg of N2 -[3(S)-[[N-[6-(benzyloxycarbonyl)-2-naphthoyl]-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide in 100 ml of isopropanol was 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 145 mg of N2 -[3(S)-[[N-(6-carboxy-2-naphthoyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide as a white solid from methanol/ethyl acetate; MS: m/e 646 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-474762cbe1a646e4b0ee944d16f7042c
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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