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

HRID 585712ノート

反応式

HRID 585712 の反応式
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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(±)-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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c23c7642d85b42419fd10dd3268f298d
出典データセット
uspto-grants-2005_08
特許番号
US06933319B2

反応ノート

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