Potassium trimethylsilanolate → N-tert-butoxycarbonylaminomethylsalicylic acid

HRID 1600403Notes

Reaction equation

HRID 1600403 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+]>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]

Participants

4

Reactant 2

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

Product 1

HCID 54424118N-tert-butoxycarbonylaminomethylsalicylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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, opencapillary, uncorrected).

Workup

  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
  10. customto afford 6.7 g

Sources & evidence

ORD record
ord-e3044df899bf4844b20a935cec123700
Source dataset
uspto-grants-1998_04
Patent number
US05744627

Reaction notes

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