Potassium Carbonate → Phenyl 3-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-5-ylcarbamate

HRID 871510Notes

Reaction equation

HRID 871510 reaction equation
[F:1][CH2:2][C:3]([C:7]1[CH:11]=[C:10]([NH2:12])[O:9][N:8]=1)([CH3:6])[CH2:4][F:5].Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[F:1][CH2:2][C:3]([C:7]1[CH:11]=[C:10]([NH:12][C:14](=[O:15])[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][N:8]=1)([CH3:6])[CH2:4][F:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 668767503-(1,3-Difluoro-2-methylpropan-2-yl)isoxazol-5-amine

Product 1

HCID 66876760Phenyl 3-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-5-ylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 161C, 3-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-5-amine (0.19 g, 1.08 mmol) was reacted with phenyl chloroformate (0.235 g, 1.5 mmol) in the presence of K2CO3 (0.276 g, 2 mmol) in THF (10 mL), and purified by silica gel chromatography with 10-25% EtOAc/hexane as eluants to afford phenyl 3-(1,3-difluoro-2-methylpropan-2-yl)isoxazol-5-ylcarbamate as solid (0.319 g, 100%). 1H NMR (300 MHz, CDCl3) δ 7.83 (s, 1H), 7.17-7.45 (m, 5H), 6.23 (s, 1H), 4.69 (dq, 2H), 4.50 (dq, 2H), 1.40 (s, 3H); LC-MS (ESI) m/z 297 (M+H)+.

Workup

  1. custompurified by silica gel chromatography with 10-25% EtOAc/hexane as eluants

Sources & evidence

ORD record
ord-1a263989af9a4e15a08d883fdb638dc5
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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