Water → 2-Benzyloxycarbonylamino-3-(6-methoxy-pyridin-3-yl)-acrylic acid methyl ester

HRID 2355904Notes

Reaction equation

[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1.[C:17]([O:20][CH2:21]C)(=[O:19])[CH3:18].[OH2:23]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:21][O:20][C:17](=[O:19])[C:18]([NH:14][C:9]([O:8][CH2:1][C:2]1[CH:5]=[CH:12][CH:11]=[CH:10][CH:3]=1)=[O:23])=[CH:15][C:12]1[CH:13]=[N:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of potassium tert-butoxide (1.23 g, 1.5 equiv) in methylene chloride (70 mL, −20° C.) was added a solution of N-benzyloxycarbonyl-α-phosphonoglycine trimethyl ester (3.63 g, 1.5 equiv) in methylene chloride (15 mL). The resulting solution was stirred 5 min and treated with the 6-methoxy-pyridine-3-carbaldehyde (1.0 g, 7.3 mmol) in methylene chloride (15 mL). After stirring for 1.5 h, the reaction was warmed to 0° C. and stirred 1 h. The reaction was quickly poured into a separatory funnel containing ethyl acetate and water. Brine was added to aid in separation of the layers. The aqueous was extracted with ethyl acetate (3×) which were in turn washed with brine, dried over magnesium sulfate, and concentrated to give 2.63 g (quant.) which was used without purification. Mass spec.: 343.08 (MH)+.

Workup

stirringAfter stirring for 1.5 h
stirringstirred 1 h
additionThe reaction was quickly poured into a separatory funnel
customto aid in separation of the layers
extractionThe aqueous was extracted with ethyl acetate (3×) which
washwashed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give 2.63 g (quant.) which
customwas used without purification

Sources & evidence

ORD record: ord-ce54e377de314e1ab605a5c31d22f2f8
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754732B2

Reaction notes

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