(Z)-Methyl 2-(benzyloxycarbonylamino)-3-(4-(tert-butoxycarbonylamino)pyridin-3-yl)acrylate → Methyl 2-(benzyloxycarbonylamino)-3-(4-(tert-butoxycarbonyl amino)pyridin-3-yl)propanoate

HRID 901210

Reaction equation

HRID 901210 reaction equation
[CH2:1]([O:8][C:9]([NH:11]/[C:12](=[CH:17]\[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])/[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[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[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 58670141(Z)-Methyl 2-(benzyloxycarbonylamino)-3-(4-(tert-butoxycarbonylamino)pyridin-3-yl)acrylate

Product 1

HCID 58670145Methyl 2-(benzyloxycarbonylamino)-3-(4-(tert-butoxycarbonyl amino)pyridin-3-yl)propanoateYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1B (1 g, 2.33 mmol) and platinium 5% wt on activated carbon (600 mg) in THF (30 mL) and MeOH (30 mL) was stirred at RT under H2 at 75 psi for 2 days. 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 methanol (0-6%) in EtOAc/hexane (1:1) to give the title compound as a white foam (360 mg, 36%). LC/MS (method A): retention time=2.77 min, (M+H)+=430.

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 methanol (0-6%) in EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-1cd83b47611a4da8bc99b274ee009557
Source dataset
uspto-grants-2008_04
Patent number
US07361766B2

Linked notes

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