Sulfuric Acid → tert-Butyl 5-oxo-L-prolinate

HRID 469727

반응식

HRID 469727 반응식
[NH:1]1[C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3][C:2]1=[O:9].[CH3:10][C:11]([CH3:13])=[CH2:12].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>ClCCl>[C:11]([O:7][C:6]([C@@H:5]1[CH2:4][CH2:3][C:2](=[O:9])[NH:1]1)=[O:8])([CH3:13])([CH3:12])[CH3:10]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 7405L-Pyroglutamic AcidHCID 8255IsobutyleneHCID 516892Sodium Bicarbonate

생성물 1

HCID 10888648tert-Butyl 5-oxo-L-prolinate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A pressure flask is charged with (S)-(−)-2-pyrrolidone-5-carboxylic acid (25 g, 193.6 mmol) and dichloromethane (100 mL) and the stirred suspension is cooled in a dry ice acetone bath. Liquid 2-methylpropene (150 mL) is added followed by concentrated sulfuric acid (0.5 mL). The pressure flask is sealed and the reaction mixture is stirred at room temperature for 48 h. The pressure flask is cooled in a dry acetone bath and the reaction mixture is diluted with dichloromethane (500 mL) and treated with a saturated solution of sodium bicarbonate until the effervescence is ceased. The organic layer is separated, washed with saturated solution of sodium bicarbonate (300 mL), brine (300 mL), dried over anhydrous Na2SO4 and solvent removed in vacuo to give the title compound as a white crystalline solid. The crude material is used without purification.

후처리

  1. temperaturethe stirred suspension is cooled in a dry ice acetone bath
  2. customThe pressure flask is sealed
  3. temperatureThe pressure flask is cooled in a dry acetone bath
  4. customThe organic layer is separated
  5. washwashed with saturated solution of sodium bicarbonate (300 mL), brine (300 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customremoved in vacuo

출처 및 근거

ORD 기록
ord-7e41d20859be4bfcb5f33e9458184f62
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629157B2

연결된 노트

불러오는 중…