Water → trans-3-methanesulfonyloxymethyl-6-cyano-3,4-dihydro-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran

HRID 487636노트

반응식

HRID 487636 반응식
O[C@@H:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:4]=2[C@H:3]1[N:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][C:17]1=[O:27].[CH2:28](N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37].[OH2:40]>C(Cl)Cl>[CH3:35][S:36]([O:38][CH2:28][C@@H:2]1[C:7]([CH3:8])([CH3:9])[O:6][C:5]2[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:4]=2[C@H:3]1[N:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][C:17]1=[O:27])(=[O:37])=[O:40]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67821434trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran

생성물 1

HCID 86747680trans-3-methanesulfonyloxymethyl-6-cyano-3,4-dihydro-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

In 7 ml of anhydrous methylene chloride, is dissolved 368 mg of trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 19. Then, 4 ml of a solution of 607 mg of triethylamine in anhydrous methylene chloride is added. Then, 4 ml of a solution of 687 mg of methanesulfonyl chloride in anhydrous methylene chloride is dropwise added at 0° C. and reacted at room temperature for 2 hours. After stopping the reaction by adding water, the reaction mixture is extracted with methylene chloride. The organic layer is washed successively with 2N aqueous solution of hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off, and the filtrate is concentrated under reduced pressure. Thus, 446 mg of trans-3-methanesulfonyloxymethyl-6-cyano-3,4-dihydro-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran is obtained.

후처리

  1. customreacted at room temperature for 2 hours
  2. customthe reaction
  3. extractionthe reaction mixture is extracted with methylene chloride
  4. washThe organic layer is washed successively with 2N aqueous solution of hydrochloric acid, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe inorganic matter is filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bf94b6676de44e4eb069db8e097f3b00
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05296492

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