3-Methoxyaniline → (s)-2-Hydroxy-n-(3-methoxy-phenyl)-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094405Notes

Reaction equation

HRID 1094405 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[N:17]=[CH:16][C:15]([CH2:18][C:19]#N)=[CH:14][CH:13]=1.C([O:26][C:27](=O)[C@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[OH:29])(=O)C>>[OH:29][C@@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27]([N:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:19][CH2:18][C:15]1[CH:16]=[N:17][C:12]([C:11]([F:22])([F:21])[F:10])=[CH:13][CH:14]=1)=[O:26]

Participants

4

Reactant 3

HCID 108243-MethoxyanilineHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-HCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 44546377(s)-2-Hydroxy-n-(3-methoxy-phenyl)-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Procedure

In analogy to example 55, 3-Methoxy-phenylamine, (6-Trifluoromethyl-pyridin-3-yl)-acetonitrile & (S)-(+)-O-acetyl-L-mandelic acid were successively coupled then hydrolysed to give the target compound. MS(m/e): 431.1 [M+H]+.

Workup

  1. customhydrolysed to give the target compound

Sources & evidence

ORD record
ord-6fb7cc9113d74b4a91e03690cc27476f
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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