Phosphate → (5R)-3-[6-(2-{[3-(Dimethylamino)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 219041

반응식

HRID 219041 반응식
[CH3:1][N:2]([CH3:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[H-].[Na+].CS(O[CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][C@@H:31]([C:33]2[CH:44]=[CH:43][C:36]3[O:37][C:38]([CH3:42])([CH3:41])[O:39][CH2:40][C:35]=3[CH:34]=2)[O:30][C:29]1=[O:45])(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C>[CH3:1][N:2]([CH3:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][O:7][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][C@@H:31]([C:33]2[CH:44]=[CH:43][C:36]3[O:37][C:38]([CH3:41])([CH3:42])[O:39][CH2:40][C:35]=3[CH:34]=2)[O:30][C:29]1=[O:45]

참가 물질

6

반응물 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 90133m-(Dimethylamino)benzyl alcoholHCID 468322282-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate

생성물 1

HCID 66845431(5R)-3-[6-(2-{[3-(Dimethylamino)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one수율 95.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 3-dimethylaminobenzyl alcohol (641 mg) in DMF (3 ml) under nitrogen was treated with sodium hydride (220 mg, 60% in oil) and the mixture stirred at 20° for 15 min. A solution of 2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate (2.00 g) in DMF (5 ml) was added and the mixture was stirred at 20° for 21 h. Phosphate buffer solution (15 ml, pH6.5) was added, the mixture stirred for 15 min and then extracted with EtOAc. The combined organic layers were washed with water, dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by Biotage (40 g). Elution with EtOAc-PE (1:2) gave the title compound (2.125 g). LCMS RT=3.47 min.

후처리

  1. stirringthe mixture was stirred at 20° for 21 h
  2. stirringthe mixture stirred for 15 min
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by Biotage (40 g)
  8. washElution with EtOAc-PE (1:2)

출처 및 근거

ORD 기록
ord-a6267eb3f35a42b59c16514eef8f203d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198483B2

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