2-Fluoro-3-phenylprop-2-enoic acid → HCID 68443237, compound

HRID 505491Notes

Reaction equation

C[O:2][C:3](=[O:29])[C@@H:4]([NH2:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[C:8]([Br:27])[CH:7]=1.[F:30][C:31](=[CH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:32](O)=[O:33]>>[Br:27][C:8]1[CH:7]=[C:6]([CH2:5][C@H:4]([NH:28][C:32](=[O:33])[C:31]([F:30])=[CH:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:3]([OH:2])=[O:29])[CH:11]=[CH:10][C:9]=1[O:12][CH2:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20]

Participants

Reactant 2

HCID 983212-Fluoro-3-phenylprop-2-enoic acid

HCID 68445645(2S)-2-Amino-3-{3-bromo-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid methyl ester

Product 1

HCID 68443237HCID 68443237, compoundYield 28%

Procedure

Following the procedures described in Example 1, Intermediate 3B was used in place of Intermediate 3A, and α-fluorocinnamic acid was used in place of cinnamic acid to give (2S)-3-{3-bromo-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-ethoxy]-phenyl}-2-(2-fluoro-3-phenyl-acryloylamino)-propionic acid as a white solid with the yield of 28% and mp: 243˜245° C.

Sources & evidence

ORD record: ord-bdf3485af665496588696eb5b5cae4ce
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781468B2

Reaction notes

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