4'-Formyl-[1,1'-biphenyl]-2-carbonitrile → HCID 22852213, compound

HRID 1609182Notes

Reaction equation

HRID 1609182 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:27])[C@H:21]([C@H:23]([CH2:25][CH3:26])[CH3:24])[NH2:22].C([BH3-])#N.[Na+]>C(OCC)(=O)C.CCCCCC>[CH3:18][O:19][C:20](=[O:27])[C@H:21]([C@H:23]([CH2:25][CH3:26])[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

5

Reactant 3

HCID 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrileHCID 5003444Sodium cyanoborohydrideHCID 11171351Isoleucine methyl ester hydrochloride

Product 1

HCID 22852213HCID 22852213, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

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, 1.76 g of (L)-isoleucine methyl ester hydrochloride and 680 mg of sodium cyanoborohydride yields N-[(2'-cyanobiphenyl-4-yl)methyl]-(L)-isoleucine methyl ester after flash chromatography (ethyl acetate/hexane 1:3). 1H-NMR (DMSO): 1.21 ppm (d, 3H), 3.63 ppm (s, 3H), 3.75 (dd, 1H), 4.56 ppm (d, 2H), 4.58 ppm (d, 2H), 5.31 ppm (t, 1H), 7.4-8 ppm aromatics.

Sources & evidence

ORD record
ord-892c6d934b85430a9f3f6de493a9418f
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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