Trifluoroacetic acid → (3R,6S)-3-Amino-1-(2-methoxyethyl)-6-phenylazepan-2-one

HRID 271909

반응식

HRID 271909 반응식
FC(F)(F)C(O)=O.[CH3:8][O:9][CH2:10][CH2:11][N:12]1[CH2:18][C@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:16][CH2:15][C@@H:14]([NH:25]C(=O)OC(C)(C)C)[C:13]1=[O:33]>ClCCl>[NH2:25][C@@H:14]1[CH2:15][CH2:16][C@@H:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:18][N:12]([CH2:11][CH2:10][O:9][CH3:8])[C:13]1=[O:33]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86595030tert-Butyl (3R,6S)-1-(2-methoxyethyl)-2-oxo-6-phenylazepan-3-ylcarbamate

생성물 1

HCID 60037849(3R,6S)-3-Amino-1-(2-methoxyethyl)-6-phenylazepan-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (2.5 mL) was added to a solution of tert-butyl (3R,6S)-1-(2-methoxyethyl)-2-oxo-6-phenylazepan-3-ylcarbamate (41 mg, 0.113 mmol) in dichloromethane (5 mL). After 1 h, the solution was concentrated. Saturated aqueous sodium bicarbonate solution was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. MS 263 (M+1). 1H NMR (500 MHz, CDCl3) δ 7.32 (t, J=7.3 Hz, 2H), 7.25-7.22 (m, 1H), 7.18 (d, J=8.3 Hz, 2H), 3.83-3.76 (m, 3H), 3.56-3.49 (m, 3H), 3.35 (s, 3H), 3.34-3.30 (m, 1H), 2.77-2.72 (m, 1H), 2.13-2.10 (m, 1H), 2.03-1.94 (m, 2H), 1.74-1.68 (m, 1H).

후처리

  1. concentrationthe solution was concentrated
  2. additionSaturated aqueous sodium bicarbonate solution was added
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. washThe combined organic extracts were washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-45d6d327719c4ebfb5e407574b917cd1
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452903B2

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