HCID 19422641, compound → N-(2'-Tert-butoxycarbonylbiphenyl-4-ylmethyl)-4-aminotetrahydropyran-4-carboxamide

HRID 744910Notes

Reaction equation

HRID 744910 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22]([C:24]2([NH:30]C(OCC3C=CC=CC=3)=O)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:23])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][C:22]([C:24]2([NH2:30])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:23])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 19422641HCID 19422641, compound

Product 1

HCID 19422624N-(2'-Tert-butoxycarbonylbiphenyl-4-ylmethyl)-4-aminotetrahydropyran-4-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product obtained in step C is dissolved in 30 ml of methanol. 400 mg of 10% palladium-on-charcoal are added and the mixture is hydrogenated at atmospheric pressure. After 1 hour, the catalyst is filtered off and the filtrate is then concentrated under vacuum. The residue is chromatographed on silica using an ethyl acetate/methanol/33% aqueous ammonia mixture (99/1/0.5; v/v/v) as the eluent to give 0.93 g of the expected product in the form of a white solid. M.p.=125°-127° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. concentrationthe filtrate is then concentrated under vacuum
  3. customThe residue is chromatographed on silica using an ethyl acetate/methanol/33% aqueous ammonia mixture (99/1/0.5

Sources & evidence

ORD record
ord-1b7704d811544405a42831a80b4ec49e
Source dataset
uspto-grants-1996_09
Patent number
US05559233

Reaction notes

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