2,2-dimethyl-2H-1,3-benzodioxol-5-amine → (s)-n-(2,2-Dimethyl-benzo[1,3]dioxol-5-yl)-2-hydroxy-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094408Notes

Reaction equation

HRID 1094408 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C:5]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:4]=2[O:3]1.[F:13][C:14]([F:25])([F:24])[C:15]1[N:20]=[CH:19][C:18]([CH2:21][C:22]#N)=[CH:17][CH:16]=1.C([O:29][C:30](=O)[C@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[OH:32])(=O)C>>[CH3:1][C:2]1([CH3:12])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]([CH2:22][CH2:21][C:18]3[CH:19]=[N:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=3)[C:30](=[O:29])[C@@H:31]([OH:32])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 3

HCID 2333172,2-dimethyl-2H-1,3-benzodioxol-5-amineHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-HCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 58007586(s)-n-(2,2-Dimethyl-benzo[1,3]dioxol-5-yl)-2-hydroxy-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Procedure

In analogy to example 55, 2,2-Dimethyl-benzo[1,3]dioxol-5-ylamine, (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): 473.1 [M+H]+.

Workup

  1. customhydrolysed to give the target compound

Sources & evidence

ORD record
ord-876bfc7ec5d84b9ba16a7e27c2209763
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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