Hydrochloric Acid → 2-(Benzoylamino)-3-(3,4-dibenzoyloxyphenyl)propanoic acid

HRID 543233

Reaction equation

[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:14])[CH:8]=1)[C:3]([OH:5])=[O:4].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>[OH-].[Na+]>[C:15]([NH:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]([O:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]=1)[C:3]([OH:5])=[O:4])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In 25 ml of 0.1N NaOH, was dissolved 2 g of 2-amino-3-(3,4-dihydroxyphenyl)propanoic acid. To the resulting solution, 3.8 ml of benzoyl chloride was added dropwise. The reaction mixture was maintained at a temperature of 0° C. for the duration of the reaction. The pH was maintained in a range of approximately by the addition of 0.2N NaOH. After about 3 hours, the reaction mixture was acidified with concentrated hydrochloric acid. The precipitate was removed by filtration and taken up in boiling carbon tetrachloride. The precipitate was then crystallized to yield a 2-(benzoylamino)-3-(3,4-dibenzoyloxyphenyl)propanoic acid.

Workup

temperatureThe pH was maintained in a range of
customThe precipitate was removed by filtration
customThe precipitate was then crystallized

Sources & evidence

ORD record: ord-bfa7835fb3624c0694dbf56fc9c550fe
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04661510

Linked notes

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