tert-butyl N-[(3S)-2-oxo-3,4-dihydro-1H-quinolin-3-yl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 87D (750 mg, 2.42 mmol) in MeOH (12 mL) and CH2Cl2 (12 mL) stirring at RT under argon was added CaCO3 (484 mg, 4.83 mmol) and benzyltrimethylammonium tribromide (1.885 g, 4.83 mmol). After 18 h, 10% aqueous NaHSO3 (5 mL) was added to the reaction mixture, and stirring was continued for 30 min. Partial evaporation under vacuum was performed to remove nearly all of the organic solvents before the mixture was extracted twice with CH2Cl2. The combined extracts were washed with water, dried (MgSO4), and evaporated under vacuum. The resulting residue was chromatographed on silica gel eluted with 25% Et2O in CH2Cl2 to obtain the title compound (746 mg) as a white foam. was continued for 30 min Partial evaporation under vacuum to remove nearly all of the organic solvents before the mixture was extracted twice with CH2Cl2 The combined extracts were washed with water dried (MgSO4) evaporated under vacuum The resulting residue was chromatographed on silica gel eluted with 25% Et2O in CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. Filtration and solvent evaporation under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. Filtration and solvent evaporation under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound, which was isolated as a side-product of the preparation of 6A, may also be prepared from 8A as follows: To a solution of 8A (750 mg, 2.42 mmol) in MeOH (12 mL) and CH2Cl2 (12 mL) stirring at RT under argon was added CaCO3 (484 mg, 4.83 mmol) and benzyltrimethylammonium tribromide (1885 mg, 4.83 mmol). After 18 h 10% aqueous NaHSO3 (5 mL) was added to the reaction mixture, and stirring was continued for 30 min. Partial evaporation under vacuum was performed to remove nearly all of the organic solvents before the mixture was extracted twice with CH2Cl2. The combined extracts were washed with water, dried (MgSO4), and evaporated under vacuum. The resulting residue was chromatographed on silica gel eluted with 25% Et2O in CH2Cl2 to obtain the title compound (746 mg) as a white foam. Partial evaporation under vacuum to remove nearly all of the organic solvents before the mixture was extracted twice with CH2Cl2 The combined extracts were washed with water dried (MgSO4) evaporated under vacuum The resulting residue was chromatographed on silica gel eluted with 25% Et2O in CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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, Peptech catalog # BL284) 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. Filtration and solvent evaporation under vacuum