Phenyl 3-isopropylisoxazol-5-ylcarbamate → Phenyl 3-cyclopropylisoxazol-5-ylcarbamate

HRID 631407Notes

Reaction equation

HRID 631407 reaction equation
C1(C2C=C(N)ON=2)CC1.[CH:10]([C:13]1[CH:17]=[C:16]([NH:18][C:19](=[O:27])[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:15][N:14]=1)([CH3:12])[CH3:11]>>[CH:10]1([C:13]2[CH:17]=[C:16]([NH:18][C:19](=[O:27])[O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:15][N:14]=2)[CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 13489689Phenyl 3-isopropylisoxazol-5-ylcarbamateHCID 162277793-Cyclopropyl-1,2-oxazol-5-amine

Product 1

HCID 59394778Phenyl 3-cyclopropylisoxazol-5-ylcarbamateYield 71%

Procedure

Prepared from 3-cyclopropylisoxazol-5-amine (300 mg, 2.42 mmol) according to the method described for phenyl 3-isopropylisoxazol-5-ylcarbamate in Example 122A Step 3, to afford phenyl 3-cyclopropylisoxazol-5-ylcarbamate as a yellow oil (420 mg, 71%). 1H NMR (300 MHz, CDCl3) δ 7.99 (brs, 1H), 7.39-7.44 (m, 2H), 7.29 (m, 1H), 7.15-7.20 (m, 2H), 5.84 (s, 1H), 1.98 (m, 1H), 1.01-1.05 (m, 2H), 0.82-0.88 (m, 2H); LC-MS (ESI) m/z 245 (M+H)+.

Sources & evidence

ORD record
ord-b3e114910e7f4f6096632b67b6b04ac3
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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