3-(2-Fluoro-4-hydroxy-phenyl)-propionic acid methyl ester → 3-[2-fluoro-4-[[4-[(2Z)-2-methoxyimino-2-(4-methoxyphenyl)ethoxy]phenyl]methoxy]phenyl]propanoic acid

HRID 922215Notes

Reaction equation

HRID 922215 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)\[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.[F:23][C:24]1[CH:29]=[C:28](O)[CH:27]=[CH:26][C:25]=1[CH2:31][CH2:32][C:33]([O:35]C)=[O:34]>>[F:23][C:24]1[CH:29]=[C:28]([O:14][CH2:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5]/[C:4](=[N:3]\[O:2][CH3:1])/[C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)=[CH:12][CH:11]=2)[CH:27]=[CH:26][C:25]=1[CH2:31][CH2:32][C:33]([OH:35])=[O:34]

Participants

3

Reactant 2

HCID 666857593-(2-Fluoro-4-hydroxy-phenyl)-propionic acid methyl esterHCID 87106073[4-[(2Z)-2-methoxyimino-2-(4-methoxyphenyl)ethoxy]phenyl]methanol

Product 1

HCID 566402073-[2-fluoro-4-[[4-[(2Z)-2-methoxyimino-2-(4-methoxyphenyl)ethoxy]phenyl]methoxy]phenyl]propanoic acidYield 71%

Procedure

Compound 40 was synthesized from (1Z)-2-[4-(hydroxy methyl)phenoxy]-1-(4-methoxyphenyl)ethanone O-methyloxime (0.25 g, 0.84 mmol) and methyl 3-(2-fluoro-4-hydroxyphenyl)propanoate (0.2 g, 0.94 mmol) by following the procedure described in scheme 18 (0.1 g, yield: 71.00%); Purity: 98.10%.

Sources & evidence

ORD record
ord-143111eab4a44c87b8400262a182f691
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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