1,1'-Biphenyl-4-yl-boronic acid → (2S)-2-{[(R)-[4-(1,1'-biphenyl-4-ylcarbonyl)phenyl](phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

HRID 1180435Notes

Reaction equation

HRID 1180435 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:9][C@@H:10]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([NH:13][CH2:14][C:15]#[N:16])=[O:12])=[CH:4][CH:3]=1.[C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C[CH2:43][O:44]C(C)=O.CCCCCC>>[C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][C:30]([C:43]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:9][C@@H:10]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([NH:13][CH2:14][C:15]#[N:16])=[O:12])=[CH:4][CH:3]=2)=[O:44])=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 10319660(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamideHCID 21226206Ethyl acetate hexane

Product 1

HCID 10098044(2S)-2-{[(R)-[4-(1,1'-biphenyl-4-ylcarbonyl)phenyl](phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

Procedure

Using the same procedures as described for the example 50, (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide (105 mg, 0.253 mmol) was reacted with 1,1′-biphenyl-4-ylboronic acid (50 mg, 0.253 mmol, 1 eg) to give the title compound after chromatography with 20% EtOAc/hexane.

Sources & evidence

ORD record
ord-bd4603a552584fde92e0cc5c56cf4186
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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