Potassium trimethylsilanolate → N-tert-butoxycarbonylaminomethylsalicylic acid

HRID 342836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342836
[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+]>O1CCCC1>[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 54424118N-tert-butoxycarbonylaminomethylsalicylic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl N-tert-butoxycarbonylaminomethylsalicylate (8.7 g, 30.9 mmoles) was dissolved in dry tetrahydrofuran (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°-144° C., decomposes with effervescence on melting, open capillary, uncorrected).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7c97720793a244edb2e71fc909831067
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859210

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