Hydrochloric Acid → HCID 22261733, compound

HRID 1610345Notes

Reaction equation

HRID 1610345 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:28])[CH:9]([NH:20]C(=O)OC(C)(C)C)[CH2:10][C:11]2[S:15][C:14]([C:16]([F:19])([F:18])[F:17])=[N:13][CH:12]=2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:20][CH:9]([CH2:10][C:11]1[S:15][C:14]([C:16]([F:19])([F:18])[F:17])=[N:13][CH:12]=1)[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 22261816HCID 22261816, compound

Product 1

HCID 22261733HCID 22261733, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl N-[(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[[2-(trifluoromethyl)-1,3-thiazol-5-yl]methyl]ethyl]carbamate (0.711 g, 1.691 mmol) and conc. hydrochloric acid (0.5 ml) in methanol (5 ml) was heated under reflux for 10 min. The reaction solution was diluted with water, alkalified with potassium carbonate and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel (APS type) column chromatography (ethyl acetate) to give the objective substance.

Workup

  1. temperatureunder reflux for 10 min
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel (APS type) column chromatography (ethyl acetate)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-12bd9fe9ecae4a31bbd2c919fce34f23
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…