6-amino-3,4-dihydro-2H-1-benzopyran-4-ol → (s)-2-Hydroxy-n-((r)-4-hydroxy-chroman-6-yl)-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094412Notes

Reaction equation

HRID 1094412 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH:5]2[OH:12].[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>>[OH:32][C@@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:30]([N:1]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C@H:5]2[OH:12])[CH2:22][CH2:21][C:18]1[CH:19]=[N:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=1)=[O:29]

Participants

4

Reactant 3

HCID 220610426-amino-3,4-dihydro-2H-1-benzopyran-4-olHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-HCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 58007578(s)-2-Hydroxy-n-((r)-4-hydroxy-chroman-6-yl)-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Procedure

In analogy to example 55, 6-Amino-chroman-4-ol (WO 2003063794), (6-Trifluoromethyl-pyridin-3-yl)-acetonitrile & (S)-(+)-O-acetyl-L-mandelic acid were successively coupled then hydrolysed to give after silica gel chromatography the target compound. MS(m/e): 473.1 [M+H]+.

Workup

  1. customhydrolysed to give after silica gel chromatography the target compound

Sources & evidence

ORD record
ord-827630d0e83f4182bf2bcc97c24cb244
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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