1-Bromo-2-methylpropane → (S)-tert-Butyl 1-isobutyl-2-oxoazepan-3-ylcarbamate

HRID 529563노트

반응식

HRID 529563 반응식
[O:1]=[C:2]1[C@@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[H-].[Na+].[CH2:19](Br)[CH:20]([CH3:22])[CH3:21].[NH4+].[Cl-]>CN(C=O)C>[CH2:19]([N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:2]1=[O:1])[CH:20]([CH3:22])[CH3:21]

참가 물질

6

반응물 4

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7022178(S)-tert-Butyl (2-oxoazepan-3-yl)carbamate

생성물 1

HCID 68310529(S)-tert-Butyl 1-isobutyl-2-oxoazepan-3-ylcarbamate수율 49%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (S)-tert-butyl 2-oxoazepan-3-ylcarbamate (116 mg, 0.510 mmol) in DMF (2 mL) at 0° C. was added sodium hydride (60% in oil, 23 mg, 0.57 mmol) in 2 portions. After stirring for 5 min, isobutyl bromide (175 mg, 1.28 mmol) was added to the reaction mixture and the mixture was stirred at rt for 20 h. Saturated aqueous NH4Cl (2 mL) was added to the mixture and crude product was extracted with methylene chloride (3 mL) and the combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified using silica gel chromatography to afford (S)-tert-Butyl 1-isobutyl-2-oxoazepan-3-ylcarbamate (46.4 mg, 0.247 mmol, 49% yield). Anal. Calcd. for C15H28N2O3 m/z 284.2. found: 285.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 6.44 (d, J=6.64 Hz, 1H), 4.26 (t, J=9 Hz, 1H), 3.57-3.50 (m, 1H), 3.26-3.17 (m, 2H), 3.10-3.05 (m, 1H), 1.84-1.62 (m, 5H), 1.37 (s, 9H), 1.34-1.24 (m, 2H), 0.84-0.80 (m, 6H).

후처리

  1. stirringthe mixture was stirred at rt for 20 h
  2. extractionwas extracted with methylene chloride (3 mL)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified

출처 및 근거

ORD 기록
ord-7bb752e53f454cb3869c006670397167
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346852B2

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