Potassium Carbonate → (S)-methyl-3-(hydroxymethyl)-4-(5-methoxypyridin-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylate

HRID 912433Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][N:12]=2)[C:5]=1[O:19][CH2:20][C@H:21]1[CH2:23][O:22]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:4]1[C:5]2[O:19][CH2:20][C@H:21]([CH2:23][OH:22])[N:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][N:12]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1)=[O:24]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (R)-methyl-3-(5-methoxypyridin-2-ylamino)-2-(oxiran-2-ylmethoxy)benzoate 0.53 g (1.6 mmol) of step 5 in dimethylformamide 5 mL was added K2CO3 0.28 g (2.0 mmol), followed by stirring at 100° C. for 5 hrs. The reaction mixture is cooled to room temperature, concentrated in a vacuum, diluted with ethylacetate, and washed with distilled water and a saturated NaCl solution. After drying over magnesium sulfate and concentration in a vacuum, purification by column chromatography (developing solvent: ethylacetate/hexane=1/1) afforded 0.50 g of the title compound (yield 94%).

Workup

temperatureThe reaction mixture is cooled to room temperature
concentrationconcentrated in a vacuum
additiondiluted with ethylacetate
washwashed with distilled water
dry with materialAfter drying over magnesium sulfate and concentration in a vacuum, purification by column chromatography (developing solvent: ethylacetate/hexane=1/1)

Sources & evidence

ORD record: ord-56c29750177b4f5f83820250116a43c1
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026235B1

Reaction notes

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