Chloroacetone → Benzyl N-[(3R)-1-acetonyl-2-oxo-4,5-dihydro-3H-1-benzazepin-3-yl]carbamate

HRID 2068540노트

반응식

HRID 2068540 반응식
[OH-].[K+].[O:3]=[C:4]1[C@H:10]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[NH:5]1.Cl[CH2:27][C:28](=[O:30])[CH3:29].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:27]([N:5]1[C:6]2[CH:25]=[CH:24][CH:23]=[CH:22][C:7]=2[CH2:8][CH2:9][C@@H:10]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:4]1=[O:3])[C:28]([CH3:29])=[O:30]

참가 물질

6

반응물 4

HCID 6571Chloroacetone2회HCID 14797Potassium Hydroxide2회HCID 2724141Tetrabutylammonium Fluoride2회HCID 58304068Benzyl N-[(3R)-2-oxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate

생성물 1

HCID 58304091Benzyl N-[(3R)-1-acetonyl-2-oxo-4,5-dihydro-3H-1-benzazepin-3-yl]carbamate수율 69.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Add powdered potassium hydroxide (KOH) (0.72 g, 12.89 mmol) to a solution of benzyl N-[(3R)-2-oxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate (2.0 g, 6.44 mmol), chloroacetone (1.19 g, 12.89 mmol), and tetrabutylammonium fluoride (1.29 mL, 1.29 mmol, 1M solution in THF) in tetrahydrofuran (65 mL). Stir the mixture for approximately 16 hours at ambient temperature. Add additional potassium hydroxide (0.361 g, 6.44 mmol), chloroacetone (0.59 g, 6.44 mmol), tetrabutylammonium fluoride (0.65 mL, 0.65 mmol, 1M solution in THF) and THF (20 mL) to the reaction and stir for approximately 48 hours at ambient temperature. Filter the reaction mixture through diatomaceous earth and concentrate the filtrate under reduced pressure. Purify the residue by flash chromatography (10% ethyl acetate/hexane to 100% ethyl acetate) to give the title compound (1.64 g, 65%): MS (m/z): 389 (M+23).

후처리

  1. customto the reaction
  2. stirringstir for approximately 48 hours at ambient temperature
  3. filtrationFilter the reaction mixture through diatomaceous earth
  4. concentrationconcentrate the filtrate under reduced pressure
  5. customPurify the residue by flash chromatography (10% ethyl acetate/hexane to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-2b6dccf1474a43aeb4047504dd16a12d
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299061B2

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