Methyl 3-cyano-3-(4-hydroxyphenyl)propanoate → 3-cyano-3-[4-[[4-[(2Z)-2-(3-fluorophenyl)-2-methoxyiminoethoxy]phenyl]methoxy]phenyl]propanoic acid

HRID 922212Notes

Reaction equation

HRID 922212 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[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.[C:22]([CH:24]([C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1)[CH2:25][C:26]([O:28]C)=[O:27])#[N:23]>>[C:22]([CH:24]([C:30]1[CH:35]=[CH:34][C:33]([O:14][CH2:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5]/[C:4](/[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)=[N:3]\[O:2][CH3:1])=[CH:12][CH:11]=2)=[CH:32][CH:31]=1)[CH2:25][C:26]([OH:28])=[O:27])#[N:23]

Participants

3

Reactant 2

HCID 66685605Methyl 3-cyano-3-(4-hydroxyphenyl)propanoateHCID 89790333[4-[(2Z)-2-(3-fluorophenyl)-2-methoxyiminoethoxy]phenyl]methanol

Product 1

HCID 566401413-cyano-3-[4-[[4-[(2Z)-2-(3-fluorophenyl)-2-methoxyiminoethoxy]phenyl]methoxy]phenyl]propanoic acidYield 18.73%

Procedure

Compound 35 was synthesized from (1Z)-1-(3-fluorophenyl)-2-[4-(hydroxymethyl)phenoxy]ethanone O-methyloxime (0.5 g, 1.8 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.372 g, 1.8 mmol) by following the procedure described in scheme 18 (0.1 g, yield: 18.73%); Purity: 95.1%.

Sources & evidence

ORD record
ord-597c5954f7a5410283cddec211d475b1
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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