(Z)-Methyl 2-(benzyloxycarbonylamino)-3-(3-(tert-butoxycarbonyl amino)-6-phenylpyridin-2-yl)acrylate → Methyl 2-(benzyloxycarbonylamino)-3-(3-(tert-butoxycarbonyl amino)-6-phenylpyridin-2-yl)propanoate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11]/[C:12](=[CH:17]\[C:18]1[C:23]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:22][CH:21]=[C:20]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:19]=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>[Pt].C1COCC1.CO>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1[C:23]([NH:24][C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])=[CH:22][CH:21]=[C:20]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:19]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
A suspension of 1F (650 mg, 1.29 mmol) and 5 wt % platinum on activated carbon (500 mg) in THF (60 mL) and MeOH (60 mL) was stirred at RT under H2 at 80 psi for 5 days. The reaction mixture was filtered through a Celite pad 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 (110 mg, 17%). LC/MS (method A): retention time=3.82 min, (M+H)+=506.
Workup
- filtrationThe reaction mixture was filtered through a Celite pad
- concentrationthe filtrate was concentrated
- customThe residue was purified by silica gel (40 g) column chromatography
- washeluting with a gradient of EtOAc (0-60%) in hexane
Sources & evidence
- ORD record
- ord-bfb895eb3a9b4b1f91208b92f3b34250
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07314882B2
Reaction notes
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