Aspirin → 3-(Benzyloxycarbonylamino)propyl 2-acetoxybenzoate

HRID 85353

반응식

HRID 85353 반응식
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.O[CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:41])=[O:8])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 2244AspirinHCID 8471Triethylamine2회HCID 10928Ethyl chloroformateHCID 562256Benzyl N-(3-hydroxypropyl)carbamate

생성물 1

HCID 591932393-(Benzyloxycarbonylamino)propyl 2-acetoxybenzoate수율 54%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a solution of 2-acetoxybenzoic acid (2.0 g, 11.1 mmol) and triethylamine (1.8 mL, 11.1 mmol) in CH2Cl2 (40 mL) at 0° C. was slowly added ClCO2Et (1.1 mL, 167 mmol). The reaction mixture was stirred (0° C., 2 h) and filtered. The filtrate was added to a solution of benzyl 3-hydroxypropylcarbamate (2.1 g, 10.0 mmol) and triethylamine (15 mL) in CH2Cl2 (40 mL). The reaction mixture was stirred (RT, 4 h) and quenched with H2O (50 mL). The organic layer was washed with 1M aqueous HCl, saturated aqueous Na2CO3 (30 mL) and H2O (50 mL). The organic solution was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography, (PE-EtOAc, 5:1) to afford 3-(benzyloxycarbonylamino)propyl 2-acetoxybenzoate (2.0 g, 54%) as a colorless oil. Mass calculated for C20H21NO64=371.38; found: [M+H]+=372.3.

후처리

  1. customat 0° C.
  2. filtrationfiltered
  3. stirringThe reaction mixture was stirred (RT, 4 h)
  4. customquenched with H2O (50 mL)
  5. washThe organic layer was washed with 1M aqueous HCl, saturated aqueous Na2CO3 (30 mL) and H2O (50 mL)
  6. dry with materialThe organic solution was dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography, (PE-EtOAc, 5:1)

출처 및 근거

ORD 기록
ord-654e6825d45e4721b19514de44dd2a1b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846972B2

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