(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid → tert-Butyl [(3S)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]carbamate

HRID 1643870Notes

Reaction equation

HRID 1643870 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-])=O)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:13][C:14]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:20][C:10]1=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 2761798(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid

Product 1

HCID 57049298tert-Butyl [(3S)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]carbamateYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound may be prepared either as described in US 2004/002495 or as follows: To a solution of (S)-2-(tert-butyloxycarbonylamino)-3-(2-nitrophenyl) propanoic acid (987 mg, 3.18 mmol) in MeOH (100 mL) was added 10% palladium on carbon (300 mg), and the mixture was stirred at RT under hydrogen at 80 psi for 24 h. Filtration and solvent evaporation under vacuum provided the title compound (800 mg) as a foam.

Workup

  1. filtrationFiltration and solvent evaporation under vacuum

Sources & evidence

ORD record
ord-2d5b7fe5541c40c09d93c44770be13d7
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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