Acetic Acid → HCID 57893114, 화합물

HRID 1511454

반응식

HRID 1511454 반응식
[CH:1]1([N+:4]#[C-:5])[CH2:3][CH2:2]1.[CH:6]1([CH2:10][C@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:12]=[O:13])[CH2:9][CH2:8][CH2:7]1.[C:22](O)(=[O:24])[CH3:23].C(OCC)(=[O:28])C>C(Cl)Cl>[C:22]([O:13][CH:12]([C@@H:11]([NH:14][C:15]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21])[CH2:10][CH:6]1[CH2:9][CH2:8][CH2:7]1)[C:5]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:28])(=[O:24])[CH3:23]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2758008IsocyanocyclopropaneHCID 57893126HCID 57893126, 화합물

생성물 1

HCID 57893114HCID 57893114, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

To a solution of cyclopropylisonitrile (1.21 g, 18 mmol), (S)-tert-butyl 1-cyclobutyl-3-oxopropan-2-ylcarbamate (2.95 g, 13 mmol) in methylene chloride(20 mL), was added acetic acid (1.56 g, 26 mmol) at 0° C. After the addition was complete, the reaction mixture was allowed to warm to 25° C. and stirred for another 4 hours. The reaction mixture was diluted with 200 mL ethyl acetate and washed with a saturated solution of sodium bicarbonate, then brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the crude product was crystallized from 50 mL of ethyl acetate and hexane (v/v=1/1) to give (3S)-3-(tert-butoxycarbonylamino)-4-cyclobutyl-1-(cyclopropylamino)-1-oxobutan-2-yl acetate (3.8 g) as a white solid.

후처리

  1. additionAfter the addition
  2. washwashed with a saturated solution of sodium bicarbonate
  3. dry with materialbrine, and dried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was crystallized from 50 mL of ethyl acetate and hexane (v/v=1/1)

출처 및 근거

ORD 기록
ord-fb0f9205ee744d33ba0aa35a4009f1d5
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211897B2

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