Pyridine → (R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester

HRID 37544

반응식

HRID 37544 반응식
[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Br:19][CH2:20][C:21](Br)=[O:22].N1C=CC=CC=1>>[CH3:7][O:6][C:4](=[O:5])[CH2:3][C@H:2]([O:1][C:21](=[O:22])[CH2:20][Br:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

4

반응물 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 98349453R-hydroxymyristic acid methyl ester

생성물 1

HCID 53830523(R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester수율 90%

실험 절차

To a rapidly-stirred slurry of 1.29 g (4.99 mmol) methyl (R)-3-hydroxytetradecanoate and 0.45 ml (5.2 mmol) bromoacetyl bromide in 25 ml hexanes at 0° C. in a flame-dried flask under N2 was added 0.42 ml (5.2 mmol)pyridine all at once. The mixture was removed from the cold bath for 30 min. The mixture was suction filtered through celite, washing with 75 ml ether. The filtrate was washed with 2×100 ml H2O and with 50 ml 10% NaHCO3. The ether was dried over MgSO4 and removed by rotary evaporation, giving 1.70 g (90%) crude (R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester as a yellow oil. Analytically pure samples could be prepared by subjecting the oil to radial chromatography, eluting with CH2Cl2.

후처리

  1. customThe mixture was removed from the cold bath for 30 min
  2. filtrationfiltered through celite
  3. washwashing with 75 ml ether
  4. washThe filtrate was washed with 2×100 ml H2O and with 50 ml 10% NaHCO3
  5. dry with materialThe ether was dried over MgSO4
  6. customremoved by rotary evaporation

출처 및 근거

ORD 기록
ord-720c99001e6e47de9d4bb6669ec93d3a
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420305

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