Hydrochloric Acid → HCID 15521369, compound

HRID 1978213Notes

Reaction equation

C([O:3][C:4](=[O:25])[CH:5]([CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.Cl>>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([S:14]([CH2:13][CH:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([OH:25])=[O:3])(=[O:16])=[O:15])=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 15521368HCID 15521368, compound

Product 1

HCID 15521369HCID 15521369, compoundYield 89.7%

Conditions

Temperature: 115 °C

Procedure

A mixture of 0.56 g (1.5 mmol) of 2-[(4-methoxybenzenesulfonyl)methyl]-3-phenyl-propanoic acid ethyl ester and 8 ml of 6N HCl is heated at 115° C. for 17 hours. The mixture is transferred to 100 ml of ice-water and extracted with two portions of ethyl acetate. The organic phase is extracted with three 50 mL portions of aqueous 5% sodium bicarbonate. The bicarbonate solution is poured over ice and acidified with concentrated HCl. The acidified aqueous mixture is extracted with three 50 mL portions of ethyl acetate and the combined organic extracts are concentrated in vacuo to yield 0.45 g of the title compound as a white solid.

Workup

extractionextracted with two portions of ethyl acetate
extractionThe organic phase is extracted with three 50 mL portions of aqueous 5% sodium bicarbonate
additionThe bicarbonate solution is poured over ice
extractionThe acidified aqueous mixture is extracted with three 50 mL portions of ethyl acetate
concentrationthe combined organic extracts are concentrated in vacuo

Sources & evidence

ORD record: ord-6a80607317084988a782e09538a27590
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235928B1

Reaction notes

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