Potassium Carbonate → (2S)-2,3-dihydro-1-[(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-yl)sulfonyl]indole-2-carboxylic acid

HRID 253164Notes

Reaction equation

HRID 253164 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[C:10]([OH:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]1([CH3:34])[CH2:25][CH2:24][C:23]2[CH:26]=[C:27]([S:30](Cl)(=[O:32])=[O:31])[CH:28]=[CH:29][C:22]=2[O:21]1>O.C(#N)C>[CH3:19][C:20]1([CH3:34])[CH2:25][CH2:24][C:23]2[CH:26]=[C:27]([S:30]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][C@H:2]3[C:10]([OH:12])=[O:11])(=[O:32])=[O:31])[CH:28]=[CH:29][C:22]=2[O:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2733920Indoline-2-carboxylic acid, (S)-HCID 27797742,2-Dimethyl-6-Chromanesulfonyl Chloride

Product 1

HCID 66845811(2S)-2,3-dihydro-1-[(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-yl)sulfonyl]indole-2-carboxylic acidYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent

Procedure

1 g (6.13 mmol) of 2,3-dihydro-(2S)-1H-indole-2-carboxylic acid, and 0.97 g (7.05 mmol) of potassium carbonate are solubilised in 2 ml of water. 1.6 g (6.13 mmol) of 3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-sulfonyl chloride solubilised in 12 ml of acetonitrile and 2 ml of water are added. Agitation is allowed to take place for 5 hours at ambient temperature. Water is added to the reaction medium, washing is performed with ethyl acetate, the acidity of the aqueous phase is raised to pH 3 by a solution of hydrochloric acid 1 N, and then extraction is performed using ethyl acetate. The organic phases are collected, dried on magnesium sulfate, filtered and concentrated under reduced pressure. The evaporation residue is purified by silica column chromatography eluting with the help of a dichloromethane/methanol (9/1; v/v) mixture. The expected product is obtained in the form of a beige foam with a yield of 73%.

Workup

  1. customfor 5 hours
  2. customat ambient temperature
  3. washwashing
  4. temperaturethe acidity of the aqueous phase is raised to pH 3 by a solution of hydrochloric acid 1 N
  5. extractionextraction
  6. customThe organic phases are collected
  7. customdried on magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe evaporation residue is purified by silica column chromatography
  11. washeluting with the help of a dichloromethane/methanol (9/1; v/v) mixture

Sources & evidence

ORD record
ord-2219d297833a45b8bd1d6439377e0d1c
Source dataset
uspto-grants-2011_01
Patent number
US07872021B2

Reaction notes

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