Potassium Carbonate → Phenyl 5-(1-(trifluoromethyl)cyclopropyl)isoxazol-3-ylcarbamate

HRID 631744Notes

Reaction equation

HRID 631744 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1([C:6]2[O:10][N:9]=[C:8]([NH2:11])[CH:7]=2)[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>ClCCl>[F:13][C:2]([F:1])([F:12])[C:3]1([C:6]2[O:10][N:9]=[C:8]([NH:11][C:21](=[O:22])[O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:7]=2)[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 668759565-(1-(Trifluoromethyl)cyclopropyl)isoxazol-3-amine

Product 1

HCID 66876669Phenyl 5-(1-(trifluoromethyl)cyclopropyl)isoxazol-3-ylcarbamateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 5-(1-(trifluoromethyl)cyclopropyl)isoxazol-3-amine (687 mg, 3.58 mmol) and potassium carbonate (987 mg, 7.0 mmol) in dry dichloromethane (30 mL) at 0° C., was added a solution of phenyl chloroformate (848 mg, 5.42 mmol) in anhydrous dichloromethane (5 mL). The reaction mixture was warmed to room temperature and stirred for a further 15 h. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give an oil. Purification via silica gel flash chromatography afforded phenyl 5-(1-(trifluoromethyl)cyclopropyl)isoxazol-3-ylcarbamate (727 mg, 65%) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) δ 11.34 (brs, 1H), 7.40-7.47 (m, 2H), 7.20-7.31 (m, 3H), 6.80 (s, 1H), 1.45-1.56 (m, 4H); LC-MS (ESI) m/z 313 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give an oil
  4. customPurification via silica gel flash chromatography

Sources & evidence

ORD record
ord-5c898fc519c444dfb6898a11c9110d11
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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