N-(tert-butoxycarbonyl)-O-(2-nitrobiphenyl-3-yl)-L-serine → O-(2-aminobiphenyl-3-yl)-N-(tert-butoxycarbonyl)-L-serine

HRID 1670435Notes

Reaction equation

HRID 1670435 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([OH:29])=[O:28])[CH2:10][O:11][C:12]1[C:13]([N+:24]([O-])=O)=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH2:24][C:13]1[C:12]([O:11][CH2:10][C@@H:9]([C:27]([OH:29])=[O:28])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:17][CH:16]=[CH:15][C:14]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 67328200N-(tert-butoxycarbonyl)-O-(2-nitrobiphenyl-3-yl)-L-serine

Product 1

HCID 67329381O-(2-aminobiphenyl-3-yl)-N-(tert-butoxycarbonyl)-L-serineYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In an autoclave containing 280 mg of 41 (0.696 mmol), 30 mg of Pd/C (10%) and 18 mL of MeOH, hydrogenation is performed at 2 bar for 10 h at 20° C. After filtration of the catalyst on celite, the solvent is evaporated and 260 mg of expected product 42 are obtained, which product is used directly for the next step.

Workup

  1. filtrationAfter filtration of the catalyst on celite
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-b8a6755a017f49c3a258ab3427707f5a
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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