(Z)-Methyl 2-(benzyloxycarbonylamino)-3-(2-(tert-butoxycarbonyl amino)-5-phenylpyridin-3-yl)acrylate → Methyl 2-(benzyloxycarbonylamino)-3-(2-(tert-butoxycarbonyl amino)-5-phenylpyridin-3-yl)propanoate

HRID 2221089Notes

Reaction equation

HRID 2221089 reaction equation
[CH2:1]([O:8][C:9]([NH:11]/[C:12](=[CH:17]\[C:18]1[C:19]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:20][CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:23]=1)/[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.CO>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1[C:19]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:20][CH:21]=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:23]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58671540(Z)-Methyl 2-(benzyloxycarbonylamino)-3-(2-(tert-butoxycarbonyl amino)-5-phenylpyridin-3-yl)acrylate

Product 1

HCID 58671546Methyl 2-(benzyloxycarbonylamino)-3-(2-(tert-butoxycarbonyl amino)-5-phenylpyridin-3-yl)propanoateYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1E (560 mg, 1.11 mmol) and 5% wt. platinium on activated carbon (500 mg) in THF (90 mL) and MeOH (90 mL) was stirred at RT under H2 at 80 psi for 2 days. After this time, no starting material was detected by LC-MS. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as a foam (420 mg, 75%). LC/MS (method A): retention time=3.24 min, (M+H)+=506.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel (40 g) column chromatography
  4. washeluting with a gradient of EtOAc (0-60%) in hexane

Sources & evidence

ORD record
ord-2054786176d140f99a2f434b2c3dfb56
Source dataset
uspto-grants-2008_05
Patent number
US07368458B2

Reaction notes

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