Benzyloxycarbonyl-asparagine → N2 [3(S)-[[N-(benzyloxy carbonyl)-L-asparaginyl]amino]-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1-tert.butyl-L-prolinamide

HRID 54072Notes

Reaction equation

HRID 54072 reaction equation
[N:1]#[N:2].C(O[C:11]([NH:13][C@@H:14]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:33][CH:32]=1)[C@H:15]([OH:29])[CH2:16][C@@:17]1([C:26]([NH2:28])=[O:27])[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([CH3:25])([CH3:24])[CH3:23])=[O:12])C1C=CC=CC=1.[CH2:42]([O:49][C:50]([NH:52][C@H:53](C(O)=O)[CH2:54][C:55](=[O:57])[NH2:56])=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(O)C.[Pd]>[N:1]#[N:2].[CH2:42]([O:49][C:50]([NH:52][C@H:53]([C:11]([NH:13][C@@H:14]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:33][CH:32]=1)[C@H:15]([OH:29])[CH2:16][C@@:17]1([C:26]([NH2:28])=[O:27])[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([CH3:25])([CH3:23])[CH3:24])=[O:12])[CH2:54][C:55](=[O:57])[NH2:56])=[O:51])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

5

Reactant 2

HCID 75314Benzyloxycarbonyl-asparagineHCID 86746230N2 [3(S)-(benzyloxyformamido)-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1-tert.butyl-L-prolinamide

Product 1

HCID 86746228N2 [3(S)-[[N-(benzyloxy carbonyl)-L-asparaginyl]amino]-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1-tert.butyl-L-prolinamideYield 31.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.58 g of N2 -[3(S)-(benzyloxyformamido)-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1 -tert.butyl-L-prolinamide in 200 ml of ethanol was hydrogenated over 100 mg of 10% palladium-on-carbon for 4 hours. The catalyst was removed by filtration and the filtrate was evaporated to give an oil which was coupled with 0.74 g 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 was obtained 0.59 g of N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-4-(4-tert.butoxyphenyl)-2(R)-hydroxybutyl]-N1 -tert.butyl-L-prolinamide as a white solid; MS: m/e 654 [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-ddea87e941b244aa99b0112d6194617a
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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