Carbon Dioxide → 3-(Tert-butoxycarbonylamino)-2-methoxyisonicotinic acid

HRID 2422677Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=[CH:5][N:4]=1.CN(C)CCN(C)C.C([Li])CCC.[C:30](=[O:32])=[O:31].[Cl-].[NH4+]>C(OCC)C>[C:12]([O:11][C:10]([NH:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][C:7]=1[C:30]([OH:32])=[O:31])=[O:16])([CH3:13])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

T-butyl (2-methoxypyridin-3-yl)carbamate (8.0 g, 35.7 mmol) and tetramethylethylenediamine (8.3 g, 71.4 mmol) were dissolved in diethyl ether (100 mL). The reaction solution was stirred at −78° C., to which n-butyllithium (2.44 M in hexane, 36.6 mL) was dropwise added at that temperature. The reaction solution was stirred at −78° C. for 1 hour, then gradually heated up to 0° C., and CO2 (solid) was added to it at 0° C. This was stirred at that temperature, and then aqueous saturated ammonium chloride solution was added thereto. The aqueous layer was separated, controlled to have a pH of 1 with 1 N hydrochloric acid added thereto, and extracted with chloroform. All the organic layers were combined, and dried with magnesium sulfate. The solvent was evaporated off under reduced pressure to obtain the intended compound (6.74 g, 70.4%) as a pale yellow oily substance.

Workup

additionwas dropwise added at that temperature
temperaturegradually heated up to 0° C.
stirringThis was stirred at that temperature
customThe aqueous layer was separated
additionadded
extractionextracted with chloroform
dry with materialdried with magnesium sulfate
customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-e20539ca3f204dad9ff6fbb918c2a918
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960394B2

Reaction notes

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