Sodium hydride → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(3-nitrobenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one

HRID 916799노트

반응식

HRID 916799 반응식
[CH3:1][C:2]1([CH3:30])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][OH:29])=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[H-].[Na+].[N+:33]([C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH2:39]Br)([O-:35])=[O:34]>CN(C=O)C>[CH3:1][C:2]1([CH3:30])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][O:29][CH2:39][C:38]5[CH:41]=[CH:42][CH:43]=[C:36]([N+:33]([O-:35])=[O:34])[CH:37]=5)=[CH:24][CH:25]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 11441342(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{2-[4-(2-hydroxyethoxy)phenyl]ethyl}-1,3-oxazolidin-2-one

생성물 1

HCID 11284238(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(3-nitrobenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{2-[4-(2-hydroxyethoxy)phenyl]ethyl}-1,3-oxazolidin-2-one (1 g) in DMF (15 mL) was treated with sodium hydride (167 mg) under nitrogen and stirred for 15 min. To this was added 3-nitrobenzyl bromide (721 mg) and the reaction mixture was stirred for 20 h. The solution was then concentrated in vacuo and the residue was taken up in EtOAc, washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (Biotage, 40 g) eluting with CH2Cl2-MeOH (500:1) and then CH2Cl2-MeOH (250:1) to give the title compound (1.22 g). LCMS RT=3.57 min.

후처리

  1. stirringthe reaction mixture was stirred for 20 h
  2. concentrationThe solution was then concentrated in vacuo
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (Biotage, 40 g)
  7. washeluting with CH2Cl2-MeOH (500:1)

출처 및 근거

ORD 기록
ord-9e3a13f2fa1b4afa9594265f47f7530d
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271197B2

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