1-[3(S)-[[N-(3-benzyloxy-2-naphthoyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide → HCID 70041000, compound

HRID 267136Notes

Reaction equation

HRID 267136 reaction equation
C([O:8][C:9]1[C:10]([C:19]([NH:21][C@H:22]([C:27]([NH:29][C@@H:30]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@H:31]([OH:46])[CH2:32][N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]2[C:39]([NH:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])=[O:20])=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)C1C=CC=CC=1>C(O)C.[Pd]>[C:42]([NH:41][C:39]([C@@H:34]1[CH2:35][CH2:36][CH2:37][CH2:38][N:33]1[CH2:32][C@@H:31]([OH:46])[C@@H:30]([NH:29][C:27](=[O:28])[C@H:22]([CH2:23][C:24](=[O:26])[NH2:25])[NH:21][C:19]([C:10]1[C:9]([OH:8])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)=[O:20])[CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

4

Reactant 1

HCID 700410141-[3(S)-[[N-(3-benzyloxy-2-naphthoyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide

Product 1

HCID 70041000HCID 70041000, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 181 mg of 1-[3(S)-[[N-(3-benzyloxy-2-naphthoyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide in 5 ml of ethanol 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. After trituration with diethyl ether there were obtained 110 mg of N-tert.butyl-1-[3(S)-[[N-(3-hydroxy-2-naphthoyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-2(S)-piperidinecarboxamide as a pale yellow solid; MS: m/e 632 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-21a58e0cd96a4ea08a540b33576ed442
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Reaction notes

Loading…