(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]-N-ethylcyclohexanecarboxamide → (+/-)-3-(2,4-Dihydroxyphenyl)-N-ethylcyclohexanecarboxamide

HRID 2307174Notes

Reaction equation

HRID 2307174 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])[CH2:16]1>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])[CH2:16]1

Participants

3

Reactant 1

HCID 22337779(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]-N-ethylcyclohexanecarboxamide

Product 1

HCID 22337813(+/-)-3-(2,4-Dihydroxyphenyl)-N-ethylcyclohexanecarboxamideYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]-N-ethylcyclohexanecarboxamide (25 mg), methanol (2 ml) and acidic ion exchange resin (300 mg) were heated to reflux for 4 hr. The reaction mixture was filtered and the resin was washed with methanol. The combined filtrate and washings were evaporated in vacuo and the crude residue was purified by preparative HPLC to furnish the title compound as a solid (2 mg, 12%). δH(CD3OD) 1.80 (3H, t), 1.30-1.60 (4H, m), 1.74-1.94 (4H, m), 2.26-2.36 (1H, m), 2.82-2.92 (1H, m), 3.16 (2H, q), 6.21-6.26 (2H, m), 6.88 (1H, d); m/z (ES+) 264 (M+H)+.

Workup

  1. temperatureto reflux for 4 hr
  2. filtrationThe reaction mixture was filtered
  3. washthe resin was washed with methanol
  4. customThe combined filtrate and washings were evaporated in vacuo
  5. customthe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5eb96ee48ca746b4b2ad56a28e84502b
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

Loading…