Hydrochloric Acid → HCID 9868574, compound

HRID 987327Notes

Reaction equation

HRID 987327 reaction equation
C([O:3][C:4](=[O:34])[C@@H:5]([O:31][CH2:32][CH3:33])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl.C(#N)C>C1COCC1.O>[CH2:32]([O:31][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:23])=[O:24])=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)[C:4]([OH:34])=[O:3])[CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 53634920HCID 53634920, compound

Product 1

HCID 9868574HCID 9868574, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-Ethoxy-3-(4-{2-[4-(phenylsulfonyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester (described in Example 89) (0.34 g; 0.70 mmole) was dissolved in THF (5 ml) and water (5 ml). Lithium hydroxide was added to the solution (0.022 g; 0.092 mmole) and the solution was stirred over night at room temperature. Aqueous hydrochloric acid was added until pH=3-4. The solvent was evaporated to a small volume. The remaining product was participated between water and diethyl ether. The water layer was once extracted with diethyl ether. The organic phase was dried with sodium sulfate and the solvent evaporated. Chromatography of the crude product, gradient eluation (99:1, 95:5 and 90:10). The product was isolated as a viscous oil. The oil was dissolved in water and acetonitrile and freezed by liquid nitrogen. Freeze-drying for 24 hours gave 0.18 g (yield 56%) of (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfonyl)phenyl]ethoxy}phenyl)propanoic acid.

Workup

  1. customThe solvent was evaporated to a small volume
  2. extractionThe water layer was once extracted with diethyl ether
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. customthe solvent evaporated
  5. customThe product was isolated as a viscous oil
  6. customFreeze-drying for 24 hours

Sources & evidence

ORD record
ord-c5c5961d9ed244c489a39aed3e4c7185
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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