Hydrochloric Acid → (Z)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylic acid

HRID 322853Notes

Reaction equation

[C:1]([NH:9]/[C:10](=[CH:15]\[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][C:17]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)/[C:11]([O:13]C)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO.O>[C:1]([NH:9]/[C:10](=[CH:15]\[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:18][C:17]=1[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)/[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl (Z)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylate (1.6 g) and aqueous potassium hydroxide in methanol (35 mL, 15%) is stirred and heated at 60° C. for 6 hours. The reaction mixture is diluted with water (20 mL), acidified to pH 1 by addition of concentrated hydrochloric acid and the resulting solid filtered. Recrystallisation fro ethyl acetate gives (Z)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylic acid (0.72 g) as a white solid, m.p. 212-213° C. [Elemental analysis:- C,75.2; H,5.28; N,2.83%. Calculated :- C,75.1; H,5.26; N,2.92%].

Workup

filtrationthe resulting solid filtered
customRecrystallisation fro ethyl acetate

Sources & evidence

ORD record: ord-9291478b848f4f9ea3fea6cb57813ff8
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211234B1

Reaction notes

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