Ethyl Acetate → HCID 69073585, compound

HRID 2101214Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH:16](P(OCC)(OCC)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:34]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41][CH:42]=O)[CH:35]=1.CCOC(C)=O>C1COCC1>[C:34]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41][CH:42]=[C:16]([CH2:15][C:12]2[CH:13]=[N:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:10][CH:11]=2)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH:35]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl 3-{6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}-2-(diethoxyphosphoryl)propanoate (1.058 g, 2.31 mmol) in dry THF (4 mL) was added to a solution of sodium hydride (0.111 g, 60% in mineral oil, 2.77 mmol) in dry TBF (3 mL) at 0° C. and the mixture was stirred at 0° C. for 60 min. To this mixture a solution of 3-(1,1′-biphenyl-3-yl)propanal (0.582 g, 2.77 mmol) in dry TBF (3 mL) was added, and the reaction mixture was allowed to attain room temperature over 22 h. EtOAc was then added, and the organic phase was washed with saturated aqueous NH4Cl and water, dried (Na2SO4) and concentrated. Flash chromatography (toluene/EtOAc, 15:1) of the residue gave tert-butyl 5-(1,1′-biphenyl-3-yl)-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)pent-2-enoate (1.105 g, 93%) as a mixture of E/Z-isomers.

Workup

waitto attain room temperature over 22 h
washthe organic phase was washed with saturated aqueous NH4Cl and water
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-27e48302a2db4a55b0da60b342de9851
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572817B2

Reaction notes

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