5-oxohexanoic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a -10° C. solution of 4-acetylbutyric acid (1 mm, 130 mg) in benzene (1.5 cc) and dichloromethane (1.5 cc) was added oxalyl chloride (1.1 mm, 140 mg) followed by a drop of N,N-dimethylformamide; the mixture was then brought to 25° C. for 30 minutes. It was then cooled to -10° C. and AlCl3 (2 mm, 266 mg) was added portion wise and the mixture held at 0° C. for 1 hour. Ice was added, followed by 1N HCl. Then the product was extracted with ethyl acetate (2×10 cc). The organic phase was washed with dilute NaHCO3 /brine and the solvents removed in vacuo to afford the title compound. the mixture held at 0° C. for 1 hour Ice was added Then the product was extracted with ethyl acetate (2×10 cc) The organic phase was washed with dilute NaHCO3 /brine the solvents removed in vacuo

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a -10° C. solution of 4-acetylbutyric acid (1 mm, 130 mg) in benzene (1.5 cc) and dichloromethane (1.5 cc) was added oxalyl chloride (1.1 mm, 140 mg) followed by a drop of N,N-dimethylformamide; the mixture was then brought to 25° C. for 30 minutes. It was then cooled to -10° C. and AlCl3 (2 mm, 266 mg) was added portion wise and the mixture held at 0° C. for 1 hour. Ice was added, followed by 1N HCl. Then the product was extracted with ethyl acetate (2×10 cc). The organic phase was washed with dilute NaHCO3 /brine and the solvents removed in vacuo to afford the title compound. the mixture held at 0° C. for 1 hour Ice was added Then the product was extracted with ethyl acetate (2×10 cc) The organic phase was washed with dilute NaHCO3 /brine the solvents removed in vacuo

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

Procedure: A solution of 65 g (0.5 mol) of 5-oxo-caproic acid and 70 g (0.51 mol) of 3-amino-4,6-dimethylaniline in 300 ml of methanol is hydrogenated at 130°-140° in the presence of Raney nickel. Yield: 110 g.

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

Procedure: A solution of 65 g (0.5 mol) of 5-oxo-caproic acid and 70 g (0.51 mol) of 3-amino-4,6-dimethylaniline in 300 ml of methanol is hydrogenated at 130°-140° in the presence of Raney nickel. Yield: 110 g.

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

Procedure: Phosphorus oxychloride (34.4 mg, 0.22 mmol) was added to a solution of [(S)-1-((R)-9-amino-5-naphthalen-1-ylmethyl-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylcarbamoyl)-ethyl]-methyl-carbamic acid tert-butyl ester (80 mg, 0.15 mmol) and 5-oxo-hexanoic acid (29.2 mg, 0.22 mmol) in pyridine (1.0 mL). After 2 h, the mixture was poured into 0.5 M HCl (5 mL) and extracted with EtOAc, the combined extracts were washed with water, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to afford the title compound. HR-MS: calcd. for C30H34N4O4S (MH+) 547.2374. found 547.2374. extracted with EtOAc the combined extracts were washed with water, brine dried over Na2SO4 filtered concentrated The residue was purified by silica gel chromatography

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 80 ml of N,N-dimethylformamide, 25 g (0.19 mol) of 5-oxohexanoic acid and 43 g (0.31 mol) of potassium carbonate were dissolved and heated at 50° C., followed by drop-wisely adding 41 g (0.29 mol) of methyl iodide and stirring at the same temperature for 2 hours. To this mixture, 150 ml of water was added, followed by extracting with diethyl ether (200 ml×4). The organic layer was washed with a saturated saline solution, followed by drying over anhydrous magnesium sulfate and concentrating under reduced pressure to obtain 24.9 g (yield: 90%) of methyl 5-oxohexanoate. by extracting with diethyl ether (200 ml×4) The organic layer was washed with a saturated saline solution by drying over anhydrous magnesium sulfate concentrating under reduced pressure