4'-(Aminomethyl)-biphenyl-2-carboxylic acid 1,1-dimethylethyl ester → 4'-[3-(t-Butoxycarbonylaminomethyl)-5-propyl-[1,2,4]-triazol-4-ylmethyl]biphenyl-2-carboxylic acid t-butyl ester

HRID 883505Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([O:26][C:27](=[O:41])[NH:28]/[C:29](=C(/OCC)\CCC)/[C:30]([NH:32][NH2:33])=O)([CH3:25])([CH3:24])[CH3:23]>C(O)C>[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][N:21]3[C:6]([CH2:8][CH2:13][CH3:12])=[N:33][N:32]=[C:30]3[CH2:29][NH:28][C:27]([O:26][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:41])=[CH:18][CH:19]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

4′-Aminomethylbiphenyl-2-carboxylic acid t-butyl ester (1.5 g, 5.2 mmol) and [1-ethoxy-but-(E)-ylidene-hydrazinocarbonylmethyl]carbamic acid t-butyl ester (1.0 g, 3.5 mmol) were combined and dissolved in ethanol (50 mL). The mixture was heated at 50° C. for 2 hours and then 70° C. overnight. The mixture was then cooled and concentrated. The product was purified by silica gel chromatography (0-20% MeOH:DCM) to obtain intermediate (23a) (400 g). MS m/z: [M+H+] calcd for C29H38N4O4, 507.6. found 507.3.

Workup

custom70° C. overnight
temperatureThe mixture was then cooled
concentrationconcentrated
customThe product was purified by silica gel chromatography (0-20% MeOH:DCM)

Sources & evidence

ORD record: ord-9b9103b15eb347d2998da85422bdf43c
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236846B2

Reaction notes

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