Hydrochloric Acid → HCID 22261532, compound

HRID 1610692Notes

Reaction equation

HRID 1610692 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:31])[CH:9]([NH:23]C(=O)OC(C)(C)C)[CH2:10][C:11]2[O:15][N:14]=[C:13]([O:16][C:17]([F:22])([F:21])[CH:18]([F:20])[F:19])[CH:12]=2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:23][CH:9]([CH2:10][C:11]1[O:15][N:14]=[C:13]([O:16][C:17]([F:21])([F:22])[CH:18]([F:19])[F:20])[CH:12]=1)[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 22261795HCID 22261795, compound

Product 1

HCID 22261532HCID 22261532, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl N-[(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[[3-(1,1,2,2-tetrafluoroethoxy)isoxazol-5-yl]methyl]ethyl]carbamate (0.291 g, 0.643 mmol) and conc. hydrochloric acid. (0.2 ml) in methanol (5 ml) was stirred at 60° C. for 0.5 hr. The reaction solution was diluted with water, alkalified with potassium carbonate, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give a crude product of (1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-[3-(1,1,2,2-tetrafluoroethoxy)isoxazol-5-yl]propan-1-ol as a white solid (0.227 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-434a639eccff42a2a67d1310a9bbccf1
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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