Dichloromethane → 4-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 25792Notes

Reaction equation

HRID 25792 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:15][CH:16]=2)[C:11]([CH:26]([OH:28])[CH3:27])=[CH:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(N(CC)CC)C>O>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:15][CH:16]=2)[C:11]([CH:26]([O:28][S:35]([CH3:34])(=[O:37])=[O:36])[CH3:27])=[CH:10][C:9]1([CH3:29])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 207603324-(1-hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 207603354-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 300 mg of 4-(1-hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (see Example 5) and 10 mL of methylene chloride was cooled to 0° C. To this mixture, 0.060 mL of methanesulfonyl chloride and 0.204 mL of triethylamine were added. The reaction mixture was allowed to stir at the same temperature for 30 minutes. The reaction was worked up by adding water, and the product was extracted with EtOAc three times. The organic layers were combined, washed sequentially with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give 344 mg of 4-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid, which was used for the next coupling reaction without further purification.

Workup

  1. extractionthe product was extracted with EtOAc three times
  2. washwashed sequentially with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-33f82501ffdb4ed5ac1c8113b3191f1f
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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