1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Benzyloxycarbonylamino-5,5-dimethyl-hept-2,6-dienoic acid methyl ester

HRID 586139Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5](P(OC)(OC)=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].[CH3:23][C:24]([CH3:30])([CH:28]=[CH2:29])[CH2:25][CH:26]=O.C1CCN2C(=NCCC2)CC1>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]([NH:6][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])=[CH:29][CH2:28][C:24]([CH3:30])([CH3:23])[CH:25]=[CH2:26]

Participants

Conditions

Temperature: 0 °C

Procedure

N-(Benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (34.3 g, 103 mmol, 1.0 equiv) was dissolved in dry THF (250 mL) and the solution was cooled to 0° C. 3,3-Dimethyl-pent-4-en-al (11.6 g, 103 mmol, 1.0 equiv) and DBU (15.5 mL, 103 mmol, 1.0 equiv) were added and the reaction mixture was stirred for 16 h. The solution was diluted with 500 mL of CH2Cl2 and washed with 1×150 mL water, and 1×150 mL brine. The organic layer was dried over Na2SO4, decanted and concentrated in vacuo to provide 2-benzyloxycarbonylamino-5,5-dimethyl-hept-2,6-dienoic acid methyl ester as a thick oil (31 g, 95% crude). The enamide is purified by flash chromatography on silica using hexanes/EtOAc as mobile phase to yield 2-benzyloxyearbonylamino-5,5-dimethyl-hept-2,6-dienoic acid methyl ester as a thick oil that solidifies on standing.

Workup

washwashed with 1×150 mL water, and 1×150 mL brine
dry with materialThe organic layer was dried over Na2SO4
customdecanted
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7581281076e84145a250a1ca57ee30d0
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936606B2

Reaction notes

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