Ethyl Acetate → 1-(3-amino-4-chlorobenzyl)-4-[[N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl]aminomethyl]piperidine

HRID 133615Notes

Reaction equation

HRID 133615 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:39]=[C:38]([F:40])[C:37]([F:41])=[CH:36][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([N+:33]([O-])=O)[CH:27]=2)[CH2:21][CH2:20]1)=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>[C].[Pd].CO>[NH2:33][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=1[Cl:32])[CH2:25][N:22]1[CH2:23][CH2:24][CH:19]([CH2:18][NH:17][C:15](=[O:16])[CH2:14][NH:13][C:11](=[O:12])[C:10]2[CH:36]=[C:37]([F:41])[C:38]([F:40])=[CH:39][C:9]=2[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 184261594-[[N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-chloro-3-nitrobenzyl)piperidine

Product 1

HCID 184262771-(3-amino-4-chlorobenzyl)-4-[[N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl]aminomethyl]piperidine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[[N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-chloro-3-nitrobenzyl)piperidine (121 mg, 0.20 mmol) with a 10% palladium carbon (85 mg), ethyl acetate (10 mL) and methanol (1 mL) was stirred at room temperature under a hydrogen atmosphere for 19 hours. The palladium catalyst was removed by filtration, and the filtrate was concentrated to thereby afford 1-(3-amino-4-chlorobenzyl)-4-[[N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl]aminomethyl]piperidine (78 mg, 68%).

Workup

  1. customThe palladium catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to thereby afford 1-(3-amino-4-chlorobenzyl)-4-[[N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl]aminomethyl]piperidine (78 mg, 68%)

Sources & evidence

ORD record
ord-471a27597da94a969363594971e5d0fb
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

Loading…