Hydrochloric Acid → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 503032노트

반응식

HRID 503032 반응식
[CH3:1][C:2]1([CH3:23])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12](O)[CH2:13][NH:14][C:15](=[O:21])[O:16]C(C)(C)C)=[CH:11][C:5]=2[CH2:4][O:3]1.[H-].[Na+].Cl>CN(C=O)C.O>[CH3:23][C:2]1([CH3:1])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:21])[NH:14][CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10881838Carbamic acid, [(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]-, 1,1-dimethylethyl ester

생성물 1

HCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one수율 95.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

tert-Butyl (2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethylcarbamate, (86.37 g) in DMF (600 ml) was added dropwise to a stirred suspension of sodium hydride (60% oil dispersion, 11.9 g) in DMF (160 ml) with cooling such that the internal temperature remained at 0° under nitrogen. The mixture was stirred at 21° for 2 h. The mixture was recooled to 0° and 2M HCl (134 ml) was added. The mixture was diluted with water and the product was extracted with EtOAc twice. The solution was washed with brine twice, dried (MgSO4) and evaporated to give the title compound (63.55 g). LCMS RT=2.66 min.

후처리

  1. temperaturewith cooling such that the internal temperature
  2. customremained at 0° under nitrogen
  3. customwas recooled to 0°
  4. extractionthe product was extracted with EtOAc twice
  5. washThe solution was washed with brine twice
  6. dry with materialdried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-584963ba9c8142c880fa22bb61504d08
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776895B2

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