Methyl 3-[2-(cyanomethyl)-4-hydroxyphenyl]propanoate → 3-[2-(cyanomethyl)-4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoic acid

HRID 922217Notes

Reaction equation

HRID 922217 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:15]1[CH:20]=[CH:19][CH:18]=[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.[C:21]([CH2:23][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])#[N:22]>>[C:21]([CH2:23][C:24]1[CH:29]=[C:28]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5]/[C:4](=[N:3]\[O:2][CH3:1])/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][CH:9]=2)[CH:27]=[CH:26][C:25]=1[CH2:31][CH2:32][C:33]([OH:35])=[O:34])#[N:22]

Participants

3

Reactant 2

HCID 66685719Methyl 3-[2-(cyanomethyl)-4-hydroxyphenyl]propanoateHCID 86695770(4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol

Product 1

HCID 566402763-[2-(cyanomethyl)-4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoic acidYield 71%

Procedure

Compound 44 was synthesized from (1Z)-2-[4-(hydroxymethyl)-phenoxy]-1-phenylethanone O-methyloxime (0.3 g, 1.28 mmol) and methyl 3-[2-(cyanomethyl)-4-hydroxyphenyl]propanoate (0.348 g, 1.28 mmol) by following the procedure described in scheme 18 (0.1 g, yield: 71.00%); Purity: 92.72%.

Sources & evidence

ORD record
ord-d9d8c419944e41cc95bc572f0462e0da
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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