Potassium trimethylsilanolate → N-tert-butoxycarbonylaminomethylsalicylic acid

HRID 362580ノート

反応式

HRID 362580 の反応式
[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]

参加物

3

反応物 2

HCID 23668039Potassium trimethylsilanolateHCID 54558375methyl N-tert-butoxycarbonylaminomethyl-salicylate

生成物 1

HCID 54424118N-tert-butoxycarbonylaminomethylsalicylic acid収率 81%

実験手順

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).

後処理

  1. additionwas added
  2. temperatureThe yellow solution was refluxed for 24 hours, during which time a tan precipitate
  3. customformed
  4. customThe mixture was evaporated to dryness
  5. dissolutionthe solid was dissolved in cold water (100 mL)
  6. temperatureThe brown solution was chilled in an ice bath
  7. customAn off-white solid precipitated during the titration
  8. filtrationThe solid was filtered
  9. washwashed with cold water
  10. dry with materialdried in vacuo over potassium hydroxide

出典と根拠

ORDレコード
ord-3758aa70a62f48ca90065857980571dc
出典データセット
uspto-grants-1999_02
特許番号
US05869623

反応ノート

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