Lithium Hydroxide → 3-[4-(2-(4-benzylsulfonylaminophenyl)ethoxy}phenyl]-2-(S)-ethoxypropanoic acid

HRID 987312Notes

Reaction equation

HRID 987312 reaction equation
C([O:3][C:4](=[O:36])[C@@H:5]([O:33][CH2:34][CH3:35])[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]([NH:22][S:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].C(OCC)(=O)C.CCCCCCC>O1CCCC1.O.ClCCl.CO>[CH2:26]([S:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][O:13][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:33][CH2:34][CH3:35])[C:4]([OH:36])=[O:3])=[CH:12][CH:11]=2)=[CH:17][CH:18]=1)(=[O:24])=[O:25])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 3939Lithium Hydroxide2×HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 696285593-[4-{2-(4-benzylsulfonylaminophenyl)ethoxy}phenyl]-2-(S)-ethoxypropanoic acid ethyl ester

Product 1

HCID 696287233-[4-(2-(4-benzylsulfonylaminophenyl)ethoxy}phenyl]-2-(S)-ethoxypropanoic acidYield 89.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

3-[4-{2-(4-Benzylsulfonylaminophenyl)ethoxy}phenyl]-2-(S)-ethoxypropanoic acid ethyl ester (described in Example 66) (0.15 g; 0.29 mmole) was dissolved in tetrahydrofuran(2 ml). Lithium hydroxide (0.0084 g; 0.35 mmole) in water (2 ml) was added. The reaction mixture was stirred at room temperature. After 6 hours, the reaction was checked by TLC (silica gel, ethyl acetate:heptane=50:50) and it was not complete. More. lithium hydroxide (approx. 0.01 g), was added the reaction mixture was stirred overnight and tetrahydrofuran was evaporated. The remaining solution was extracted with diethyl ether. The water phase was acidified with hydorchloric acid (1%) to pH˜2 and extracted twice with ethyl acetate. The organic phases were combined, dried with magnesium sulfate and the solvent was evaporated. Chromatography of the residue on silica gel (Isolute, SI) using dichloromethane and then dichloromethane:methanol (98:2) as eluant gave 0.125 g (88% yield) of 3-[4-{2-(4-benzylsulfonylaminophenyl)ethoxy}phenyl]-2-(S)-ethoxypropanoic acid.

Workup

  1. stirringwas stirred overnight
  2. customtetrahydrofuran was evaporated
  3. extractionThe remaining solution was extracted with diethyl ether
  4. extractionextracted twice with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2b8da4d715984777b1a83a56a80de114
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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