Potassium trimethylsilanolate → HCID 54082100, compound

HRID 1274536Notes

Reaction equation

HRID 1274536 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([OH:20])=[C:12]([CH:17]=[CH:18][CH:19]=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][C:10]1[C:11]([OH:20])=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 69733477HCID 69733477, compound

Product 1

HCID 54082100HCID 54082100, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl N-tert-butoxycarbonylaminomethyl-2-hydroxybenzoate (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-butoxycarbonylaminomethyl-2-hydroxybenzoic acid (m.p. 141-144° C., decomposes with effervescence on melting, open capillary, 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

Sources & evidence

ORD record
ord-3b3a23610b5a4efca847a634a1754942
Source dataset
uspto-grants-2000_12
Patent number
US06156884

Reaction notes

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