Water → 1-benzyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid

HRID 2421885Notes

Reaction equation

[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][C:10]2[N:15]=[CH:16][C:17]([C:19]([O:21]C)=[O:20])=[CH:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>CO>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][C:10]2[N:15]=[CH:16][C:17]([C:19]([OH:21])=[O:20])=[CH:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product from Step 1 was dissolved in MeOH (1 mL) and water (0.5 mL) and placed in a 2 mL microwave vial with a magnetic stirrer bar. Lithium hydroxide (40 mg, 0.96 mmol) was added to the vial. The vial was capped and vortexed to dissolve the LiOH, and the reaction was heated for 5 minutes at 100° C. under microwave irradiation. The reaction was quenched by the addition of aqueous 1M HCl (960 μL). The volatiles were evaporated to dryness. This yielded a white/yellow solid which was used without further purification. LCMS (+ESI) m/z=285.0 [M+H]+.

Workup

customThe vial was capped
customThe reaction was quenched by the addition of aqueous 1M HCl (960 μL)
customThe volatiles were evaporated to dryness
customThis yielded a white/yellow solid which
customwas used without further purification

Sources & evidence

ORD record: ord-f01c71af4ffc46aaaacabc4998b8a35b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960377B2

Reaction notes

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