HCID 20576746, compound → HCID 67526838, compound

HRID 133756Notes

Reaction equation

HRID 133756 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[F:13])[CH3:2].[CH3:15][C:16]1[CH:17]=[C:18]([NH:25][C:26]([C:28]2([CH3:31])[CH2:30][O:29]2)=[O:27])[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23]>>[CH2:1]([O:3][C:4](=[O:14])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:31][C:28]([OH:29])([C:26](=[O:27])[NH:25][C:18]2[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:16]([CH3:15])[CH:17]=2)[CH3:30])=[CH:8][C:7]=1[F:13])[CH3:2]

Participants

3

Reactant 2

HCID 20576746HCID 20576746, compoundHCID 714200032-Methyl-N-(3-methyl-4-nitrophenyl)oxirane-2-carboxamide

Product 1

HCID 67526838HCID 67526838, compound

Procedure

{2-Fluoro-4-[2-hydroxy-2-(3-methyl-4-nitrophenylcarbamoyl)propoxy]-phenyl}carbamic acid ethyl ester was prepared as described in Example 1 starting from (2-fluoro-4-hydroxyphenyl)carbamic acid ethyl ester and 2-methyloxirane-2-carboxylic acid (3-methyl-4-nitrophenyl)amide. The crude product was purified by flash chromatography (dichloromethane-1.8% methanol). 1H NMR (400 MHz, DMSO-d6): 1.20 (3H, t, J=7.0 Hz), 1.43 (3H, s), 2.53 (3H, s), 3.97 (1H, d, J=9.7 Hz), 4.07 (2H, q, J=7.0 Hz), 4.22 (1H, d, J=9.7 Hz), 6.21 (1H, s), 6.71-6.73 (1H, m), 6.83-6.87 (1H, m), 7.31-7.35 (1H, m), 7.86-8.05 (3H, m), 8.95 (1H, s), 10.12 (1H, s).

Workup

  1. customThe crude product was purified by flash chromatography (dichloromethane-1.8% methanol)

Sources & evidence

ORD record
ord-990414cc786649f4925dcefa4c69195b
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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