3,4-Dimethylaniline → (s)-n-[2-(5-Chloro-pyridin-2-yl)-ethyl]-n-(3,4-dimethyl-phenyl)-2-hydroxy-2-phenyl-acetamide

HRID 1094413Notes

Reaction equation

HRID 1094413 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH2:9])=[N:6][CH:7]=1.[CH3:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[CH3:18])[NH2:14].C([O:22][C:23](=O)[C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25])(=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:14]([C:13]2[CH:15]=[CH:16][C:17]([CH3:18])=[C:11]([CH3:10])[CH:12]=2)[C:23](=[O:22])[C@@H:24]([OH:25])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 72483,4-DimethylanilineHCID 155476265-Chloro-2-ethenylpyridineHCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 44546442(s)-n-[2-(5-Chloro-pyridin-2-yl)-ethyl]-n-(3,4-dimethyl-phenyl)-2-hydroxy-2-phenyl-acetamide

Procedure

In analogy to example 25 step 1 and 26 step 1-2, [2-(5-Chloro-pyridin-2-yl)-ethyl]-(3,4-dimethyl-phenyl)-amine obtained by reacting 5-Chloro-2-vinyl-pyridine (CAS: 223445-06-5) with 3,4-dimethylaniline was coupled with (S)-(+)-O-acetyl-L-mandelic acid then hydrolysed to provide the title compound. MS(m/e): 395.1 [M+H]+.

Sources & evidence

ORD record
ord-11cda96bc6324d039e9dfc47a97d2dd9
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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