Dimethyl Sulfate → (R)-N-benzyl-2-(ethoxycarbonylamino)-3-methoxypropionamide

HRID 74117노트

반응식

HRID 74117 반응식
[CH2:1]([NH:8][C:9](=[O:19])[C@H:10]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](OCC)(=O)C.S(OC)(OC)(=O)=O.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([NH:8][C:9](=[O:19])[C@H:10]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][O:12][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 53344986(R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide

생성물 1

HCID 53344987(R)-N-benzyl-2-(ethoxycarbonylamino)-3-methoxypropionamide수율 70.96%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

실험 절차

To a 500 mL three-neck round bottom flask, 7.2 g (0.027 mol) (R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide, 300 mL ethyl acetate, 27.2 g (0.216 mol) dimethyl sulfate, and 2.0 g tetrabutylammonium bromide were added in sequence. At a normal temperature, 24.8 g 50% potassium hydroxide (0.2214 mol) solution was added. After the reaction was completed, 100 mL water was added, and the mixture was stirred for several minutes, and stood for layering. An organic layer was separated, and washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was evaporated, to obtain a transparent oily substance, which was triturated with n-hexane, suction-filtered, washed, and dried, to obtain a white solid of 5.37 g (0.01916 mol). The molar yield was 70.96%.

후처리

  1. customAn organic layer was separated
  2. washwashed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto obtain a transparent oily substance, which
  6. customwas triturated with n-hexane
  7. filtrationsuction-filtered
  8. washwashed
  9. customdried
  10. customto obtain a white solid of 5.37 g (0.01916 mol)

출처 및 근거

ORD 기록
ord-97cd46039495446584bca2082a5cf2de
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829226B2

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