2,4-Dimethylpyridine → N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-L-valine methyl ester

HRID 875172Notes

Reaction equation

HRID 875172 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH:21]([CH3:23])[CH3:22])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])=[CH:9][CH:8]=1.[CH3:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30].N1C(C)=CC=CC=1C.N1C=CC(C)=CC=1C.N1C=CC=C(C)C=1C.N1C=CC(C)=C(C)C=1.N1C=C(C)C=CC=1C.N1C=C(C)C=C(C)C=1>>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH:21]([CH3:22])[CH3:23])[N:5]([C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])=[CH:9][CH:8]=1

Participants

9

Reactant 8

HCID 79362,4-DimethylpyridineHCID 79372,6-LutidineHCID 114173,4-DimethylpyridineHCID 114202,3-LutidineHCID 115262,5-DimethylpyridineHCID 115653,5-DimethylpyridineHCID 61186Valeryl chlorideHCID 16744794N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl ester

Product 1

HCID 16744795N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-L-valine methyl ester

Procedure

Reacting pure N-[(2′-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester (VI) with n-valeryl chloride in the presence of a heterocyclic amine base selected from 2,6-lutidine, 2,4-lutidine, 2,3-lutidine, 3,4-lutidine, 2,5-lutidine, 3,5-lutidine to produce pure N-valeryl-N-[(2′-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester (VII) substantially free from alkene impurity of formula (VIIa).

Sources & evidence

ORD record
ord-5a43a3ecd81a419d85e3afee1e8cc43b
Source dataset
uspto-grants-2015_03
Patent number
US08981109B2

Reaction notes

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