rac-methyl (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylate → trans-(1R,2R)-2-[4-[[4-[(2Z)-2-methoxyimino-2-(2-methylphenyl)ethoxy]phenyl]methylamino]phenyl]cyclopropane-1-carboxylic acid

HRID 922196Notes

Reaction equation

HRID 922196 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.[CH3:15][O:16]/[N:17]=[C:18](/[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])\[CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>>[CH3:15][O:16]/[N:17]=[C:18](/[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])\[CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]3[CH2:10][C@H:9]3[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 68667437rac-methyl (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylateHCID 871061194-[(2Z)-2-methoxyimino-2-(2-methylphenyl)ethoxy]benzaldehyde

Product 1

HCID 56639928trans-(1R,2R)-2-[4-[[4-[(2Z)-2-methoxyimino-2-(2-methylphenyl)ethoxy]phenyl]methylamino]phenyl]cyclopropane-1-carboxylic acidYield 28%

Procedure

Compound 15 was synthesized from methyl (1R,2R)-2-(4-aminophenyl)cyclopropane carboxylate (0.18 g, 0.9 mmol) and 4-{[(2Z)-2-(methoxyimino)-2-(2-methylphenyl)ethyl]oxy}benzaldehyde (0.31 g, 1.1 mmol) by following the procedure described in Scheme 3 (0.12 g, yield: 28%); Purity: 91.26%.

Sources & evidence

ORD record
ord-1afc7c4e8ceb4ee7baae3de37df1b9bc
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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