Methyl valinate hydrochloride → N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl ester

HRID 1739074Notes

Reaction equation

HRID 1739074 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)#[N:2].Cl.[CH3:18][O:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:25])[CH3:24])[NH2:22].C([BH3-])#N.[Na+]>>[CH3:18][O:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:25])[CH3:24])[NH:22][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N:2])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 111190Methyl valinate hydrochlorideHCID 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrileHCID 5003444Sodium cyanoborohydride

Product 1

HCID 16744794N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl ester

Procedure

Reaction of 0.5 g of 2'-cyanobiphenyl-4-carbaldehyde, 2.5 g of molecular sieve 5 A, 0.815 g of (L)-valine methyl ester hydrochloride and 180 mg of sodium cyanoborohydride yields N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester after flash chromatography (N3). (TLC: N3) Rf : 0.5.

Sources & evidence

ORD record
ord-23f252f6a1104d2b935dc17345f5a9c9
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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