Benzyl chloroformate → 4-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acid

HRID 1432413

반응식

HRID 1432413 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH2:5]([O:4][C:2]([NH:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 1715604-Aminocyclohexanecarboxylic acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 2852474-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acid수율 59.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
0 °C

실험 절차

Benzyl chloroformate (2.2 mL, 15.4 mmol) was added to a solution of 4-amino-cyclohexanecarboxylic acid (2 g, 14.0 mmol) in a mixture of 1,4-dioxane (5 mL) and saturated sodium bicarbonate aqueous solution (5 mL). The mixture was stirred at 0° C. for 3 hours. Dioxane was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate solution was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 2.3 g (59%) of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid as yellow oil. MS (ESP−) m/z 276.39 (M−1). 1H NMR (300 MHz, CDCl3) δ 7.34 (m, 5H), 5.09 (s, 2H), 2.24 (m, 1H), 2.04 (m, 2H), 1.83 (m, 2H), 1.44 (m, 3H), 0.97 (m, 2H).

후처리

  1. customDioxane was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6c69283da5d7425f8e8e14bb48941e17
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612094B2

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