Phosphoric Acid → 2(4-Fluorophenyl)5-benzoxazole acetic acid

HRID 1906553Notes

Reaction equation

HRID 1906553 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([CH:17](C)[C:18]([OH:20])=[O:19])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.OC1C=CC(CC(O)=O)=CC=1N.FC1C=CC(C(Cl)=O)=CC=1.P(=O)(O)(O)O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 1004Phosphoric AcidHCID 399402-(2-(4-Fluorophenyl)-1,3-benzoxazol-5-yl)propanoic acidHCID 678794-Fluorobenzoyl chlorideHCID 1473103(3-Amino-4-hydroxyphenyl)acetic acid

Product 1

HCID 202122952(4-Fluorophenyl)5-benzoxazole acetic acid

Procedure

A process for preparing 2(4-fluorophenyl)α-methyl-5-benzoxazole acetic acid starting from 4-hydroxy-3-amino-phenylacetic acid, which is firstly reacted with 4-fluorobenzoyl chloride, and the product obtained is reacted with phosphoric acid; the 2(4-fluorophenyl)5-benzoxazole acetic acid obtained in this manner is esterified with ethyl alcohol, and the ester is treated with diethyloxalate; the ethyl 2(4-fluorophenyl)5-benzoxazole oxalacetate obtained is reacted with formaldehyde and potassium carbonate to obtain ethyl 2(4-fluorophenyl)5-benzoxazole acrylate, which is hydrolysed to obtain the corresponding acid, from which the 2(4-fluorophenyl)α-methyl-5-benzoxazole acetic acid is obtained by hydrogenation.

Workup

  1. customthe product obtained

Sources & evidence

ORD record
ord-f67684f9f97940a5abcdcacea1dd932a
Source dataset
uspto-grants-1987_03
Patent number
US04652654

Reaction notes

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