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

HRID 922230Notes

Reaction equation

HRID 922230 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.[CH:21]1([CH2:24][O:25][C:26]2[CH:31]=[C:30](O)[CH:29]=[CH:28][C:27]=2[CH2:33][CH2:34][C:35]([O:37]C)=[O:36])[CH2:23][CH2:22]1>>[CH:21]1([CH2:24][O:25][C:26]2[CH:31]=[C:30]([O:14][CH2:13][C:10]3[CH:11]=[CH:12][C:7]([O:6][CH2:5]/[C:4](=[N:3]\[O:2][CH3:1])/[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:8][CH:9]=3)[CH:29]=[CH:28][C:27]=2[CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 66686064Methyl 3-[2-(cyclopropylmethoxy)-4-hydroxyphenyl]propanoateHCID 86695770(4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol

Product 1

HCID 871060063-[2-(cyclopropylmethoxy)-4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoic acidYield 4.2%

Procedure

Compound 58 was synthesized from (1Z)-2-[4-(hydroxymethyl)phenoxy]-1-phenylethanone O-methyloxime (0.656 g, 2.4 mmol) and methyl 3-[2-(cyclopropylmethoxy)-4-hydroxyphenyl]propanoate (0.6 g, 2.4 mmol) by following the procedure described in scheme 18 (0.04 g, yield: 4.20%); Purity: 98.15%.

Sources & evidence

ORD record
ord-5dc8592fce6f48598c1313af372ed977
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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