2,2,2-Trifluoroethanol → HCID 178446405, 화합물

HRID 579585

반응식

HRID 579585 반응식
[CH2:1]([N:8]([CH:16]1[CH2:19][CH:18]([C:20](=O)[CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:17]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([N+:30]#[C-])([CH3:29])([CH3:28])[CH3:27].[C:32]([O-:35])(=O)[CH3:33].[NH4+:36].FC(F)(F)[CH2:39][OH:40]>C(OCC)(=O)C>[C:32]([NH:36][C:20]([C@@H:18]1[CH2:19][C@H:16]([N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13])[CH2:17]1)([CH2:21][CH2:22][CH:23]=[CH2:24])[C:39]([NH:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:40])(=[O:35])[CH3:33]

참가 물질

6

반응물 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 66833494Tert-butyl benzyl(3-pent-4-enoylcyclobutyl)carbamate

생성물 1

HCID 178446405HCID 178446405, 화합물수율 83%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of tert-butyl benzyl(3-pent-4-enoylcyclobutyl)carbamate (7.7 g, 21.1 mmol, 5 eq), t-butyl isonitrile (12 mL, 106 mmol, 10 eq) and ammonium acetate (16.3 g, 212 mmol) in 2,2,2-trifluoroethanol (24 mL, 0.9 M) was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, quenched with 2 M HCl and extracted with ethyl acetate. The organic layer was washed successively with 2 M HCl and sat'd aq sodium chloride, dried over MgSO4, filtered and concentrated. Purification by column chromatography (ethyl acetate in hexanes) gave cis-tert-butyl 3-(2-acetamido-1-(tert-butylamino)-1-oxohex-5-en-2-yl)cyclobutyl(benzyl)carbamate as a yellow solid (8.9 g, 17.5 mmol, 83%). 1H NMR (CDCl3, 300 MHz) δ 7.32-7.10 (m, 6H), 6.08 (brs, 1H), 5.80-5.64 (m, 1H), 5.01-4.87 (m, 2H), 4.42 (brs, 2H), 4.41-4.08 (m, 1H), 2.79-2.58 (m, 1H), 2.40-1.99 (m, 8H), 1.98-1.80 (m, 3H), 1.56-1.08 (m, 18H), ESI MS found for C28H43N3O4 m/z [508.2 (M+23)] and trans-tert-butyl 3-(2-acetamido-1-(tert-butylamino)-1-oxohex-5-en-2-yl)cyclobutyl(benzyl)carbamate as a white foam (1.1 g, 2.2 mmol, 10%). 1H NMR (CDCl3, 300 MHz) δ 7.32-7.11 (m, 5H), 6.79 (brs, 1H), 5.83-5.68 (m, 1H), 5.56 (brs, 1H), 5.02-4.88 (m, 2H), 4.54-4.37 (m, 2H), 4.35-4.16 (m, 1H), 2.94-2.75 (m, 2H), 2.51-2.39 (m, 1H), 2.38-2.19 (m, 2H), 2.18-1.90 (m, 5H), 1.86-1.70 (m, 1H), 1.67-1.58 (m, 1H), 1.47-1.22 (m, 18H), ESI MS found for C28H43N3O4 m/z [486.5 (M+1), 508.0 (M+23)].

후처리

  1. customquenched with 2 M HCl
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with 2 M HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-8e8a33cfb5634a6fb556e70db89f2f6e
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

연결된 노트

불러오는 중…