Sodium Hydroxide → 1-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 1878719Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([C:20]([O:22]C)=[O:21])=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([C:20]([OH:22])=[O:21])=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of methyl 1-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylate (3600 mg, 10.6 mmol) in THF (10 mL) and MeOH (5 mL) was added NaOH (3181 μl, 31.8 mmol). The solution was stirred at 23° C. for 48 h and was partitioned between CH2Cl2 and 10% citric acid (aq. pH˜4). The aqueous was extracted with CH2Cl2 (3×50 mL). The combined organics were dried with brine and MgSO4, and concentrated to a yellow solid under reduced pressure. MS (ESI pos. ion) m/z (MH+): 326. Calc'd exact mass for C16H27NO4Si: 325.

Workup

customwas partitioned between CH2Cl2 and 10% citric acid (aq. pH˜4)
extractionThe aqueous was extracted with CH2Cl2 (3×50 mL)
dry with materialThe combined organics were dried with brine and MgSO4
concentrationconcentrated to a yellow solid under reduced pressure

Sources & evidence

ORD record: ord-4098a795ccf54aa6b5c527b6baccd6ca
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314087B2

Reaction notes

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