Potassium trimethylsilanolate → N-tert-butoxycarbonylaminomethylsalicylic acid
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][O:10][C:11]1[C:12](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:13]([O:15]C)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[O-].[K+]>>[C:1]([O:5][C:6]([NH:8][CH2:9][O:10][C:11]1[C:12](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
Methyl N-tert-butoxycarbonylaminomethylsalicylate (8.7 g, 30.9 mmoles) was dissolved in dry tetrahydroflran (100 mL), and potassium trimethylsilanolate (4.4 g, 30.9 mmoles, 90% pure) was added. The yellow solution was refluxed for 24 hours, during which time a tan precipitate formed and the solvent turned light brown. The mixture was evaporated to dryness, and the solid was dissolved in cold water (100 mL). The brown solution was chilled in an ice bath, and saturated aqueous potassium hydrogen sulfate solution was used to titrate the stirred solution to pH 2-3. An off-white solid precipitated during the titration. The solid was filtered, washed with cold water, and dried in vacuo over potassium hydroxide to afford 6.7 g, (81% yield) of crude N-tert-butoxycarbonylaminomethylsalicylic acid (m.p. 141°-1449 C., decomposes with effervescence on melting, open capillary, uncorrected).
Workup
- additionwas added
- temperatureThe yellow solution was refluxed for 24 hours, during which time a tan precipitate
- customformed
- customThe mixture was evaporated to dryness
- dissolutionthe solid was dissolved in cold water (100 mL)
- temperatureThe brown solution was chilled in an ice bath
- customAn off-white solid precipitated during the titration
- filtrationThe solid was filtered
- washwashed with cold water
- dry with materialdried in vacuo over potassium hydroxide
Sources & evidence
- ORD record
- ord-3758aa70a62f48ca90065857980571dc
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869623
Reaction notes
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