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

HRID 2307173노트

반응식

HRID 2307173 반응식
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]([NH2:23])=[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]([NH2:23])=[O:22])[CH2:16]1

참가 물질

3

반응물 1

HCID 22337819(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamide

생성물 1

HCID 22337782(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanecarboxamide수율 31.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamide (22 mg), methanol (2 ml) and acidic ion exchange resin (300 mg) were heated to reflux for 5 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 give the title compound as a white solid (5 mg, 31%). δH(CD3OD) 1.45-1.82 (6H, m), 2.07-2.19 (2H, m), 2.62-2.69 (1H, m), 3.00-3.09 (1H, m), 6.20-6.28 (2H, m), 6.89 (1H, d); m/z (ES+) 236 (M+H)+.

후처리

  1. temperatureto reflux for 5 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

출처 및 근거

ORD 기록
ord-22eb919ac6a64676997a8de0ca9711e6
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828460B2

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