5-methyloxolan-2-one

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

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

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

Procedure: coli MBX769 carrying the plasmid pFS16 (FIG. 2), which permitted the expression of the Clostridium kluyveri 4-hydroxybutyryl-CoA transferase, was precultured at 37° C. in 100 mL of LB medium containing 100 μg/mL sodium ampicillin in a 250-mL Erlenmeyer flask with shaking at 200 rpm. The cells were centrifuged at 5000 g for 10 minutes to remove them from the LB medium after 16 hours, and they were resuspended in 100 mL of a medium containing, per liter: 4.1 or 12.4 g sodium 4-hydroxyvalerate (4HV); 5 g/L sodium 4-hydroxybutyrate (4HB); 2 g glucose; 2.5 g LB broth powder (Difco; Detroit, Mich.); 50 mmol potassium phosphate, pH7; 100 μg/mL sodium ampicillin; and 0.1 mmol isopropyl-β-D-thiogalactopyranoside (IPTG). The sodium 4-hydroxyvalerate was obtained by saponification of γ-valerolactone in a solution of sodium hydroxide. The cells were incubated in this medium for 3 days with shaking at 200 rpm at 32° C. in the same flask in which they had been precultured. When 4.1 g/L sodium 4-hydroxyvalerate was present initially, the cells accumulated a polymer to 52.6% of the dry cell weight that consisted of 63.4% 3HB units and 36.6% 4HB units but no 4HV units. was precultured at 37° C. in 100 mL of LB medium to remove them from the LB medium after 16 hours containing, per liter

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

Procedure: Part A. A solution of γ-valerolactone (25.0 g, 0.249 mol) in toluene (50 mL) and n-heptylamine (35.96 g, 0.312 mol) was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate (300 mL), washed with 1N aqueous HCl (50 mL), water, brine, dried over magnesium sulfate and concentrated to give a white solid. The product was crystallized from ethyl ether:hexane to give N-heptyl-5-hydroxypentanamide (41.8 g, 0.194 mol) as white plates, mp 55°-6°. 1H NMR (CDCl3) δ6.06(bs,1H), 3.61(t,2H), 3.24(q,2H), 3.19(bs,1H), 2.19(t,2H), 1.80-1.23(m,14H), 0.866(t,3H). to reflux for 18 hours under a nitrogen atmosphere washed with 1N aqueous HCl (50 mL), water, brine dried over magnesium sulfate concentrated to give a white solid The product was crystallized from ethyl ether

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

Procedure: Part A. A solution of γ-valerolactone (25.0 g, 0.249 mol) in toluene (50 mL) and n-heptylamine (35.96 g, 0.312 mol) was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate (300 mL), washed with 1N aqueous HCl (50 mL), water, brine, dried over magnesium sulfate and concentrated to give a white solid. The product was crystallized from ethyl ether:hexane to give N-heptyl-5-hydroxypentanamide (41.8 g, 0.194 mol) as white plates, mp 55°-6°. 1H NMR (CDCl3) δ 6.06(bs,1H), 3.61(t,2H), 3.24 (q, 2H), 3.19 (bs, 1H), 2.19 (t, 2H), 1.80-1.23 (m, 14H), 0. 866 (t, 3H). to reflux for 18 hours under a nitrogen atmosphere washed with 1N aqueous HCl (50 mL), water, brine dried over magnesium sulfate concentrated to give a white solid The product was crystallized from ethyl ether

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

Procedure: 5.3 g. (0.05 mole) 4-amino-1-methylpiperidine are heated with 5.4 ml. (0.06 mole) γ-valerolactone for 48 hours at 90° C. The reaction mixture is dissolved in 50 ml. water and shaken up with methylene chloride. The aqueous phase is rendered alkaline with potassium carbonate and extracted with n-butanol. The crude base is dissolved in ethanol, 3 g. oxalic acid are added thereto, insolubles are filtered off and the filtrate is distilled off. There are obtained 8.5 g. of the oxalate of the title compound in the form of a viscous, semi-solid product. Yield 56% of theory. The reaction mixture is dissolved in 50 ml extracted with n-butanol The crude base is dissolved in ethanol oxalic acid are added insolubles are filtered off the filtrate is distilled off There are obtained 8.5 g

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

Procedure: 5-Aminooxyvaleric acid is prepared in the same manner using the procedure of Preparation 6 for 4-aminooxybutyric acid except that the γ-butyrolactone is replaced by γ-valerolactone.

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

Procedure: 5-Aminooxyvaleric acid is prepared in the same manner using the procedure of Preparation 6 for 4-aminooxybutyric acid except that the γ-butyrolactone is replaced by γ-valerolactone.

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of gamma-valerolactone (40 g.), ethyl 2-(3,4-dichlorophenylamino)-nicotinate (20 g.) and potassium t-butoxide (30 g.) was warmed in an atmosphere of nitrogen to 110° C. and kept there for 5 hr. After cooling somewhat the product was poured into 1000 ml. of 5% KOH solution and was allowed to stir overnight. The basic solution was extracted with ether (2×500 ml.) and the aqueous solution was acidified to pH 5 with conc. HCl. The solid was filtered off, washed with water, dried in air then recrystallized from methanol/charcoal to yield the desired product, m.p. 232°-234° C. After cooling somewhat the product was poured into 1000 ml The basic solution was extracted with ether (2×500 ml.) The solid was filtered off washed with water dried in air then recrystallized from methanol/charcoal

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

Procedure: Part A. A solution of γ-valerolactone (25.0 g, 0.249 mol) in toluene (50 mL) and n-heptylamine (35.96 g, 0.312 mol) was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate (300 mL) and washed with 1 N aqueous HCl (50 mL), water and brine. The organic layer was dried over magnesium sulfate and then concentrated to give a white solid. The product was crystallized from ethyl ether:hexane to give N-heptyl-5-hydroxypentanamide (41.8 g, 0.194 mol) as white plates, mp 55°-56°. 1H NMR (CDCl3) δ6.06 (bs,1H), 3.61 (t,2H,J=7.3 Hz), 3.24 (quartet,2H,J=8.4 Hz), 3.19 (bs,1H), 2.19 (t,2H,J=8.3 Hz), 1.80-1.23 (m,14H), 0.86 (t,3H,J=6.0 Hz). to reflux for 18 hours under a nitrogen atmosphere washed with 1 N aqueous HCl (50 mL), water and brine The organic layer was dried over magnesium sulfate concentrated to give a white solid The product was crystallized from ethyl ether

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

Procedure: Part A. A solution of γ-valerolactone (25.0 g, 0.249 mol) in toluene (50 mL) and n-heptylamine (35.96 g, 0.312 mol) was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate (300 mL) and washed with 1 N aqueous HCl (50 mL), water and brine. The organic layer was dried over magnesium sulfate and then concentrated to give a white solid. The product was crystallized from ethyl ether:hexane to give N-heptyl-5-hydroxypentanamide (41.8 g, 0.194 mol) as white plates, mp 55°-56°. 1H NMR (CDCl3) δ6.06 (bs,1H), 3.61 (t,2H,J=7.3 Hz), 3.24 (quartet,2H,J=8.4 Hz), 3.19 (bs,1H), 2.19 (t,2H,J=8.3 Hz), 1.80-1.23 (m,14H), 0.86 (t,3H,J=6.0 Hz). to reflux for 18 hours under a nitrogen atmosphere washed with 1 N aqueous HCl (50 mL), water and brine The organic layer was dried over magnesium sulfate concentrated to give a white solid The product was crystallized from ethyl ether

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

Procedure: Salicylaldehyde (15.2 g) and γ-valerolactone (25 g) were dissolved in toluene (150 ml). By the reactions as in the same manner as in Example 307, the title compound (17 g) was obtained, melting point 112–114° C.