HCID 86603411, compound → HCID 66716659, compound

HRID 1994483Notes

Reaction equation

HRID 1994483 reaction equation
[CH2:1]([O:8][C:9](=[O:45])[N:10]([CH2:33][CH:34]([N:42]=[N+]=[N-])[C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[C:22]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[CH:25]=[CH:24][C:23]=1[O:31][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.O=[Pt]=O>[CH2:1]([O:8][C:9](=[O:45])[N:10]([CH2:33][CH:34]([NH2:42])[C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[CH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[CH:14][C:13]=1[C:22]1[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[CH:25]=[CH:24][C:23]=1[O:31][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86603411HCID 86603411, compound

Product 1

HCID 66716659HCID 66716659, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl[2-azido-2-(4-chlorophenyl)ethyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (30 mg, 0.05 mmol) in THF (1 mL) was added PtO2 (8 mg) and the reaction was stirred at room temperature under hydrogen for 1 hour. The catalyst was removed by filtration through a plug of Celite with 100% EtOAc and the filtrate was concentrated to afford crude benzyl[2-amino-2-(4-chlorophenyl)ethyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate. Rf=0.66 (25% EtOAc/hexanes). LCMS=611.3 (M+1)+.

Workup

  1. customThe catalyst was removed by filtration through a plug of Celite with 100% EtOAc
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-429b00b8dd2d47869814c11f23b44d02
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

Loading…