2,2,2-Trifluoroethanol → HCID 86665797, 화합물

HRID 590759

반응식

HRID 590759 반응식
[CH2:1]([CH:4]1[C:8](=O)[CH2:7][CH:6]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5]1)[CH:2]=[CH2:3].[C:21]([O-:24])(=O)[CH3:22].[NH4+:25].[C:26]([N+:30]#[C-])([CH3:29])([CH3:28])[CH3:27].FC(F)(F)[CH2:34][OH:35]>>[C:21]([NH:25][C@:8]1([C:34](=[O:35])[NH:30][C:26]([CH3:29])([CH3:28])[CH3:27])[C@@H:4]([CH2:1][CH:2]=[CH2:3])[CH2:5][C@H:6]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)(=[O:24])[CH3:22]

참가 물질

5

반응물 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 67513633Benzyl 3-allyl-4-oxocyclopentylcarbamate

생성물 1

HCID 86665797HCID 86665797, 화합물수율 23%

실험 절차

A stirred mixture of benzyl 3-allyl-4-oxocyclopentylcarbamate, mixture of isomers (5.19 g, 19 mmol) and ammonium acetate (5.86 g, 76 mmol) in 2,2,2-trifluoroethanol (20 mL) under nitrogen was treated with t-butylisonitrile (6.50 mL, 57 mmol) and stirred at room temperature for 3 days. The reaction mixture was concentrated in vacuo, dissolved in dichloromethane and added to a silica gel column (˜550 cc). Successive elution with 60%, 70%, and 80% ethyl acetate/heptane afforded the subject compound together with an undesired isomer (total 3.48 g). Recrystallization (2 crops) from minimum acetonitrile/ether gave the subject compound (1.83 g, 23%) as a white solid. NMR (CDCl3): δ 7.38 (br s, 5 H), 7.10 (br s, 1 H), 5.65-5.80 (m, 1 H), 5.67 (br s, 1 H), 4.95-5.15 (m, 4 H), 4.25-4.35 (m, 1 H), 2.85-3.00 (m, 1 H), 2.60-2.70 (m, 1 H), 2.20-2.35 (m, 2 H), 1.85-2.15 (m, 3 H), 2.03 (s, 3 H), 1.40 (s, 9 H). MS (M+1): 416.1.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in dichloromethane
  3. additionadded to a silica gel column (˜550 cc)
  4. washSuccessive elution with 60%, 70%, and 80% ethyl acetate/heptane
  5. customafforded the subject compound together with an undesired isomer (total 3.48 g)
  6. customRecrystallization (2 crops) from minimum acetonitrile/ether

출처 및 근거

ORD 기록
ord-1973deb85fcc431c93e7a72451b5aca2
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233985B2

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