Water → 2-Ethoxy-3-(4-{2-[4-(2-propanesulfonyloxy)phenyl]ethoxy}phenyl)propanoic acid ethyl ester

HRID 987253Notes

Reaction equation

HRID 987253 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:33])[CH:12]([O:30][CH2:31][CH3:32])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:16][CH:15]=1)[CH3:9].[CH:34]([S:37](Cl)(=[O:39])=[O:38])([CH3:36])[CH3:35].O>ClCCl>[CH2:8]([O:10][C:11](=[O:33])[CH:12]([O:30][CH2:31][CH3:32])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][S:37]([CH:34]([CH3:36])[CH3:35])(=[O:39])=[O:38])=[CH:27][CH:28]=2)=[CH:16][CH:15]=1)[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 54239207HCID 54239207, compound

Product 1

HCID 865950602-Ethoxy-3-(4-{2-[4-(2-propanesulfonyloxy)phenyl]ethoxy}phenyl)propanoic acid ethyl esterYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.64 g; 6.28 mmole) was slowly added to a solution of 2-ethoxy-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester (1.5 g; 4.18 mmole) in dry dichloromethane (20 ml). After cooling to 0° C. isopropylsulfonyl chloride (0.9 g; 6.28 mmole) was added slowly. The reaction mixture was stirred over night at room temperature, water was added and the mixture was extracted with dichloromethane. The organic phase was washed with hydrochloric acid (1M) and sodium bicarbonate solution, dried (magnesium sulfate) and evaporated in vacuo to give 1.75 g (yield 90%) of 2-ethoxy-3-(4-{2-[4-(2-propanesulfonyloxy)phenyl]ethoxy}phenyl)propanoic acid ethyl ester.

Workup

  1. additionwas added slowly
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic phase was washed with hydrochloric acid (1M) and sodium bicarbonate solution
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4fdfdc209e8c45d3a1980db436027294
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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