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 487636Notes

Reaction equation

HRID 487636 reaction equation
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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bf94b6676de44e4eb069db8e097f3b00
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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