Methyl 3-(4-Hydroxy-2-methoxyphenyl)propanoate → 3-[4-[[4-[(2Z)-2-(4-cyanophenyl)-2-methoxyiminoethoxy]phenyl]methoxy]-2-methoxyphenyl]propanoic acid

HRID 922216Notes

Reaction equation

HRID 922216 reaction equation
[OH:1][CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8]/[C:9](/[C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)=[N:10]\[O:11][CH3:12])=[CH:5][CH:4]=1.O[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34]C)=[O:33])=[C:26]([O:36][CH3:37])[CH:25]=1>>[C:17]([C:16]1[CH:15]=[CH:14][C:13](/[C:9](=[N:10]/[O:11][CH3:12])/[CH2:8][O:7][C:6]2[CH:5]=[CH:4][C:3]([CH2:2][O:1][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[C:26]([O:36][CH3:37])[CH:25]=3)=[CH:22][CH:21]=2)=[CH:20][CH:19]=1)#[N:18]

Participants

3

Reactant 2

HCID 66685654Methyl 3-(4-Hydroxy-2-methoxyphenyl)propanoateHCID 897902314-[(Z)-C-[[4-(hydroxymethyl)phenoxy]methyl]-N-methoxycarbonimidoyl]benzonitrile

Product 1

HCID 566402103-[4-[[4-[(2Z)-2-(4-cyanophenyl)-2-methoxyiminoethoxy]phenyl]methoxy]-2-methoxyphenyl]propanoic acidYield 71.5%

Procedure

Compound 43 was synthesized from 4-{(1Z)-2-[4-(hydroxymethyl)-phenoxy]-N-methoxyethanimidoyl}benzonitrile (0.563 g, 1.9 mmol) and methyl 3-(4-hydroxy-2-methoxyphenyl)propanoate (0.4 g, 1.9 mmol) by following the procedure described in scheme 18 (0.27 g, yield: 71.5%); Purity: 94.96%.

Sources & evidence

ORD record
ord-e50757432d824895b3594e31b352a210
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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