n-(2-Fluoro-4-hydroxyphenyl)acetamide → 3-(4-Acetylamino-3-fluorophenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

HRID 133733

Reaction equation

HRID 133733 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:12])[CH3:11].[CH3:13][C:14]1[CH:15]=[C:16]([NH:23][C:24]([C:26]2([CH3:29])[CH2:28][O:27]2)=[O:25])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21]>>[C:10]([NH:9][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:29][C:26]([OH:27])([CH3:28])[C:24]([NH:23][C:16]2[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:14]([CH3:13])[CH:15]=2)=[O:25])=[CH:7][C:2]=1[F:1])(=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 190616n-(2-Fluoro-4-hydroxyphenyl)acetamideHCID 714200032-Methyl-N-(3-methyl-4-nitrophenyl)oxirane-2-carboxamide

Product 1

HCID 675259953-(4-Acetylamino-3-fluorophenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

Procedure

The compound was synthesised according to the procedure described in Example 1c. N-(2-Fluoro-4-hydroxyphenyl)acetamide (0.5 g, 3.0 mmol) and 2-methyloxirane-2-carboxylic acid (3-methyl-4-nitrophenyl)amide (0.6 g, 2.5 mmol) was used as starting materials. The product was crystallised from the mixture of ethyl acetate and diethyl ether (1:1). The yield was 0.39 g. 1H NMR (DMSO-d6): 1.42 (3H, s), 2.02 (3H, s), 2.53 (3H, s), 3.97 (1H, d, J=9.7 Hz), 4.21 (1H, d, J=9.7 Hz), 6.23 (1H, bs), 6.72 (1H, m), 6.90 (1H, m), 7.56 (1H, m), 7.88 (1H, dd, J=9.0 Hz and 2.2 Hz), 7.93 (1H, d, J=2.2 Hz), 8.03 (1H, d, J=9.0 Hz), 9.51 (1H, s), 10.15 (1H, bs).

Workup

  1. customThe compound was synthesised
  2. customThe product was crystallised from the mixture of ethyl acetate and diethyl ether (1:1)

Sources & evidence

ORD record
ord-ab10673be06549db8bbb1953dc7807b0
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Linked notes

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