Phenyl 3-isopropylisoxazol-5-ylcarbamate → Phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate

HRID 871328Notes

Reaction equation

HRID 871328 reaction equation
[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH2:10])[O:7][N:6]=1)([CH3:4])[CH3:3].C(C1C=C(N[C:20](=[O:28])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)ON=1)(C)C>>[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:20](=[O:28])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:7][N:6]=1)([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 13489689Phenyl 3-isopropylisoxazol-5-ylcarbamateHCID 534020703-(2-Fluoropropan-2-yl)-1,2-oxazol-5-amine

Product 1

HCID 66876626Phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamateYield 68%

Procedure

Prepared from 3-(2-fluoropropan-2-yl)isoxazol-5-amine (4.83 g, 33.54 mmol) according to the method described for phenyl 3-isopropylisoxazol-5-ylcarbamate in Example 122A Step 3, to afford phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate as a colorless solid (6.04 g, 68%). 1H NMR (300 MHz, CDCl3) δ 7.80 (brs, 1H), 7.39-7.45 (m, 2H), 7.18-7.32 (m, 3H), 6.27 (s, 1H), 1.74 (d, J=21 Hz, 6H); LC-MS (ESI) m/z 265 (M+H)+.

Sources & evidence

ORD record
ord-965c1d03049045ae8b17798b3fa5d8c2
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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