4-Methylmorpholine → 2-[N-(alpha-(Isopropylthio)-N-(benzyloxycarbonyl)-glycinyl)amino]benzophenone

HRID 1080377노트

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HRID 1080377 반응식
[CH:1]([S:4][CH:5]([C:17]([OH:19])=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])([CH3:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[NH2:35][C:36]1[CH:49]=[CH:48][CH:47]=[CH:46][C:37]=1[C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:39]>C(Cl)Cl>[CH:1]([S:4][CH:5]([C:17]([NH:35][C:36]1[CH:49]=[CH:48][CH:47]=[CH:46][C:37]=1[C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:39])=[O:19])[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 760802-AminobenzophenoneHCID 11346620Acetic acid, [(1-methylethyl)thio][[(phenylmethoxy)carbonyl]amino]-

생성물 1

HCID 138095072-[N-(alpha-(Isopropylthio)-N-(benzyloxycarbonyl)-glycinyl)amino]benzophenone

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

α-(isopropylthio)-N-(benyloxycarbonyl)glycine 22B was dissolved in methylene chloride (200 mL) under nitrogen atmosphere at 0° C. in a three necked flask carrying an additional funnel. To the stirred solution was added N-methylmorpholine (2.11 mL, 19.3 mmol) followed by isobutylchloroformate (2.48 mL, 19.2 mmol). This was stirred for 15 minutes at 0° C. and then heated to reflux. To the refluxing reaction mixture was added a solution of 2-aminobenzophenone 23 (3.59 g, 18.19 mmol) in dry methylene chloride (26 mL) over 20 minutes. The reaction mixture was stirred for 20 more minutes after the addition and then left stirring overnight at room temperature. The reaction mixture was washed with 10% citric acid, saturated sodium bicarbonate solution and brine, then dried over magnesium sulphate. Solvent evaporated at reduced pressure to give 9.30 g of the crude product 24. This was used without further purification.

후처리

  1. temperatureheated to reflux
  2. customTo the refluxing reaction mixture
  3. stirringThe reaction mixture was stirred for 20 more minutes
  4. additionafter the addition
  5. waitleft
  6. stirringstirring overnight at room temperature
  7. washThe reaction mixture was washed with 10% citric acid, saturated sodium bicarbonate solution and brine
  8. dry with materialdried over magnesium sulphate
  9. customSolvent evaporated at reduced pressure

출처 및 근거

ORD 기록
ord-53a3846f38d14093aec7ce51113d2a2f
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05580979

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