4'-Formyl-[1,1'-biphenyl]-2-carbonitrile → HCID 53822382, compound

HRID 1609183Notes

Reaction equation

HRID 1609183 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]([CH2:23][CH2:24][CH3:25])[NH2:22].C([BH3-])#N.[Na+]>>[CH3:18][O:19][C:20](=[O:26])[C@H:21]([CH2:23][CH2:24][CH3:25])[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 14118488methyl (2S)-2-aminopentanoate hydrochloride

Product 1

HCID 53822382HCID 53822382, compound

Procedure

The starting material can be obtained, for example, analogously to Example 1b): The reaction of 2.0 g of 2'-cyanobiphenyl-4-carbaldehyde, 9.6 g of molecular sieve 5 A, 1.34 g of (L)-norvaline methyl ester hydrochloride and 680 mg of sodium cyanoborohydride yields N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-norvaline methyl ester after flash chromatography (N3). 1H-NMR (DMSO): 0.83 ppm (t, 3H), 1.33 ppm (m, 2H), 1.55 ppm (m, 2H), 3.62 ppm (s, 3H), 3.1 ppm (m, 1H), 7.3-8 ppm aromatics.

Sources & evidence

ORD record
ord-698205c45a3a4e6e9357f4106b28a3da
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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