Hydrochloric Acid → (2S)-2-Ethoxy-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoic acid

HRID 970032Notes

Reaction equation

HRID 970032 reaction equation
[OH-].[Li+].[CH2:3]([O:5][C@@H:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:24][CH:23]=2)=[CH:15][CH:14]=1)[C:7]([O:9]CC)=[O:8])[CH3:4].Cl>C1COCC1.O>[CH2:3]([O:5][C@@H:6]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:26][CH:27]=2)=[CH:17][CH:18]=1)[C:7]([OH:9])=[O:8])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86607017ethyl(2S)-2-ethoxy-3-[4-(2-[4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoate

Product 1

HCID 11211977(2S)-2-Ethoxy-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (27 mg, 1.15 mmol) was added to a solution of ethyl(2S)-2-ethoxy-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoate (167 mg, 0.38 mmol) in THF/water 4:1 (5 mL). The reaction mixture was stirred at room temperature overnight and 1 M HCl (2 mL) was added. The THF was removed under reduced pressure. The aqueous phase was diluted with water and extracted three times with CH2Cl2 in a Phase Separator. The combined organic layers were evaporated. The residue was purified by preparative HPLC to give the product as a colorless oil (129 mg, 83%).

Workup

  1. customThe THF was removed under reduced pressure
  2. additionThe aqueous phase was diluted with water
  3. extractionextracted three times with CH2Cl2 in a Phase Separator
  4. customThe combined organic layers were evaporated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c29b94ca3fbb4a178a87b40ad58dd59e
Source dataset
uspto-grants-2007_12
Patent number
US07309720B2

Reaction notes

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