Sodium hydride → 3-Bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one

HRID 279837

반응식

HRID 279837 반응식
[Br:1][CH:2]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:11].I[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[H-].[Na+].[NH4+].[Cl-]>C1COCC1>[Br:1][CH:2]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:3]1=[O:11]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11021060Tert-butyl 2-iodoacetateHCID 136083253-Bromoperhydroazonin-2-one

생성물 1

HCID 136083263-Bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Add a solution of 7.35 g. 3-bromoperhydroazonin-2-one [Nagasawa et al., J. Med. Chem., 14, 501 (1971)]and 8.47 g t-butyl iodoacetate in 70 ml THF to a suspension of 0.881 g sodium hydride in 35 ml THF. After 2 hours at room temperature, add 15 ml saturated NH4Cl solution, filter and concentrate the filtrate in vacuo. Partition the residue between ether and H2O and wash the organic phase with H2O and brine. Dry the ether solution and filter. Decolorize the filtrate with charcoal, filter and concentrate the filtrate in vacuo to isolate 3-bromo-1-t-butoxycarbonylmethylperhydroazonin-2-one. Purify a sample for characterization by silica gel chromatography. Anal. C14H24BrNO3). Calc: C, 50.31; H, 7.24; N, 4.18; Br, 23.91. Found: C, 49.86; H, 7.33; N, 4.30; Br, 23.51. Mass spectrum: M+ at 334; m/e: 278 (M+ --C 4 H8); 261 (M+ --C4H9O); 232 (M+ --C4H9CO2 --H, base).

후처리

  1. additionAdd a solution of 7.35 g
  2. filtrationfilter
  3. concentrationconcentrate the filtrate in vacuo
  4. customPartition the residue between ether and H2O
  5. washwash the organic phase with H2O and brine
  6. dry with materialDry the ether solution
  7. filtrationfilter
  8. filtrationfilter
  9. concentrationconcentrate the filtrate in vacuo

출처 및 근거

ORD 기록
ord-496d2f3dec224346987cdee929704801
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587238

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