4'-Formyl-[1,1'-biphenyl]-2-carbonitrile → N-[(2′-Cyano[1,1′-biphenyl]-4-yl)methyl]-D-valine methyl ester

HRID 1739077Notes

Reaction equation

HRID 1739077 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 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrileHCID 5003444Sodium cyanoborohydrideHCID 11984198Methyl D-valinate hydrochloride

Product 1

HCID 29924795N-[(2′-Cyano[1,1′-biphenyl]-4-yl)methyl]-D-valine methyl ester

Procedure

Reaction of 4.0 g of 2'-cyanobiphenyl-4-carbaldehyde, 19.3 g of molecular sieve 5 A, 3.8 g of (D)-valine methyl ester hydrochloride and 1.43 g of sodium cyanoborohydride yields N-[(2'-cyanobiphenyl-4-yl)methyl]-(D)-valine methyl ester after flash chromatography (N3). (TLC: N2) Rf : 0.56.

Sources & evidence

ORD record
ord-088f2fe0bb5947c89d7c8761e9c44ac3
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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