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

HRID 1670431Notes

Reaction equation

HRID 1670431 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:17]([N+:18]([O-])=O)=[CH:16][CH:15]=[CH:14][C:13]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CCO>[NH2:18][C:17]1[C:12]([O:11][CH2:10][C@@H:9]([C:27]([OH:29])=[O:28])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[C:13]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 67328913N-(tert-butoxycarbonyl)-O-(3-nitrobiphenyl-2-yl)-L-serine

Product 1

HCID 67328341O-(3-aminobiphenyl-2-yl)-N-(tert-butoxycarbonyl)-L-serineYield 61.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In an autoclave containing 500 mg of 35 (1.243 mmol), 54 mg of Pd/C (10%) and 33 mL of EtOH, hydrogenation is performed at 2 bar for 10 h at 20° C. After filtration of the catalyst on celite, the solvent is evaporated and 284 mg of expected product 36 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-02980f861faf4b6789885f50f1edf354
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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