Phenyl 3-isopropylisoxazol-5-ylcarbamate → Phenyl 5-(1-hydroxy-2-methylpropan-2-yl)isoxazol-3-ylcarbamate

HRID 1917871Notes

Reaction equation

HRID 1917871 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:11])([CH3:10])[CH2:8][OH:9])[O:4][N:3]=1.C(C1C=C(N[C:21](=[O:29])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)ON=1)(C)C>>[OH:9][CH2:8][C:7]([C:5]1[O:4][N:3]=[C:2]([NH:1][C:21](=[O:29])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 13489689Phenyl 3-isopropylisoxazol-5-ylcarbamateHCID 534063292-(3-Amino-1,2-oxazol-5-yl)-2-methylpropan-1-ol

Product 1

HCID 66794275Phenyl 5-(1-hydroxy-2-methylpropan-2-yl)isoxazol-3-ylcarbamateYield 72%

Procedure

Prepared from 2-(3-aminoisoxazol-5-yl)-2-methylpropan-1-ol (100 mg, 0.60 mmol) according to the method described for phenyl 3-isopropylisoxazol-5-ylcarbamate in Example 122A Step 3, to afford phenyl 5-(1-hydroxy-2-methylpropan-2-yl)isoxazol-3-ylcarbamate as a colorless solid (120 mg, 72%). 1H NMR (300 MHz, CDCl3) δ 8.30 (brs, 1H), 7.42-7.43 (m, 2H), 7.26 (m, 1H), 7.18-7.21 (m, 2H), 6.65 (s, 1H), 3.67 (s, 2H), 1.98 (brs, 1H), 1.32 (s, 6H).

Sources & evidence

ORD record
ord-829571a10b224c03a7e01c9f05b035ca
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

Loading…