hept-6-enoic 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:; See reaction.notes.procedure_details.

Procedure: A solution of L-t-leucine methyl ester (1.00 g, 6.89 mmol), 6-heptenoic acid (1.06 g, 8.26 mmol), EDC (1.58 g, 8.26 mmol) and HOAt (1.23 g, 8.26 mmol) in DMF (10 mL) was stirred at RT for 2 hours. The reaction mixture was diluted with aqueous saturated NaHCO3 (30 mL), and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×30 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica (5-50% EtOAc/hexane), to give the title compound (1.42 g). LRMS (ESI) m/z 256.3 [(M+H)+; calcd for C14H26NO3: 256.2]. extracted with EtOAc (3×50 mL) The combined organic layers were washed with water (3×30 mL), brine (20 mL) dried over Na2SO4 filtered concentrated The residue was chromatographed on silica (5-50% EtOAc/hexane)

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

Procedure: A solution of L-t-leucine methyl ester (1.00 g, 6.89 mmol), 6-heptenoic acid (1.06 g, 8.26 mmol), EDC (1.58 g, 8.26 mmol) and HOAt (1.23 g, 8.26 mmol) in DMF (10 mL) was stirred at 22° C. for 2 hours. The reaction mixture was diluted with aqueous saturated NaHCO3 (30 mL), and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×30 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 5-50% EtOAc/hexane, to give the title product (1.42 g, 81%). LRMS (ESI) m/z 256.3 [(M+H)+; calcd for C14H26NO3: 256.2]. extracted with EtOAc (3×50 mL) The combined organic layers were washed with water (3×30 mL), brine (20 mL) dried over Na2SO4 filtered concentrated The residue was chromatographed on silica gel eluting with 5-50% EtOAc/hexane

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

Procedure: A solution of L-tert-leucine methyl ester (1.00 g, 6.89 mmol), 6-heptenoic acid (1.06 g, 8.26 mmol), EDC (1.58 g, 8.26 mmol) and HOAt (1.23 g, 8.26 mmol) in DMF (10 mL) was stirred at 22° C. for 2 hours. The reaction mixture was diluted with aqueous saturated NaHCO3 (30 mL), and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×30 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 5-50% EtOAc/hexane, to give the title product (1.42 g, 81%). LRMS (ESI) m/z 256.3 [(M+H)+; calcd for C14H26NO3: 256.2]. extracted with EtOAc (3×50 mL) The combined organic layers were washed with water (3×30 mL), brine (20 mL) dried over Na2SO4 filtered concentrated The residue was chromatographed on silica gel eluting with 5-50% EtOAc/hexane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 6-heptenoic acid (4.71 g, 36.75 mmol) in AcOEt (80 mL) at 0° C. were successively added triethylamine (15.3 mL, 110.24 mmol), benzyl bromide (13.1 mL, 110.24 mmol) and Bu4NI (6.79 g, 18.37 mmol). The reaction mixture was stirred at 0° C. for 2H and concentrated in vacuo. The residue is taken up in AcOEt, the organic phase was washed with a saturated aqueous NaHCO3 and H2O. The organic phase was dried over MgSO4 and the solvent removed in vacuo. Flash chromatography of the residue on silica gel (n-heptane/EtOAc, 9:1) provided compound C-9 (6.00 g 75%) as a colorless oil. 13C-NMR (62.89 MHz, CDCl3): 24.42, 28.34, 33.37, 34.13, 66.08, 114.73, 128.19, 128.55, 136.16, 138.37, 173.43. at 0° C. concentrated in vacuo the organic phase was washed with a saturated aqueous NaHCO3 and H2O The organic phase was dried over MgSO4 the solvent removed in vacuo Flash chromatography of the residue on silica gel (n-heptane/EtOAc, 9:1) provided compound C-9 (6.00 g 75%) as a colorless oil

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

Procedure: To a solution of 6-heptenoic acid (251 μL, 1.85 mmol) in CH2Cl2 (5 mL) at rt was added oxalyl chloride (476 μL, 5.55 mmol) and DMF (1 drop). After stirring for 1 hr, the reaction mixture was concentrated under reduced pressure and put under high vacuum for 15 min. The residual yellow oil was dissolved in CH2Cl2 (3 mL) and used as a stock solution (0.62M) for the subsequent acylation reactions. the reaction mixture was concentrated under reduced pressure put under high vacuum for 15 min The residual yellow oil was dissolved in CH2Cl2 (3 mL)

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

Procedure: To a solution of 6-heptenoic acid (251 μL, 1.85 mmol) in CH2Cl2 (5 mL) at rt was added oxalyl chloride (476 μL, 5.55 mmol) and DMF (1 drop). After stirring for 1 hr, the reaction mixture was concentrated under reduced pressure and put under high vacuum for 15 min. The residual yellow oil was dissolved in CH2Cl2 (3 mL) and used as a stock solution (0.62M) for the subsequent acylation reactions. the reaction mixture was concentrated under reduced pressure put under high vacuum for 15 min The residual yellow oil was dissolved in CH2Cl2 (3 mL)

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

Procedure: A solution of L-t-leucine methyl ester (1.00 g, 6.89 mmol), 6-heptenoic acid (1.06 g, 8.26 mmol), EDC (1.58 g, 8.26 mmol) and HOAt (1.23 g, 8.26 mmol) in DMF (10 mL) was stirred at RT for 2 hours. The reaction mixture was diluted with aqueous saturated NaHCO3 (30 mL), and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×30 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica (5-50% EtOAc/hexane), to give the title compound (1.42 g). LRMS (ESI) m/z 256.3 [(M+H)+; calcd for C14H26NO3: 256.2]. extracted with EtOAc (3×50 mL) The combined organic layers were washed with water (3×30 mL), brine (20 mL) dried over Na2SO4 filtered concentrated The residue was chromatographed on silica (5-50% EtOAc/hexane)

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

Procedure: A solution of L-t-leucine methyl ester (1.00 g, 6.89 mmol), 6-heptenoic acid (1.06 g, 8.26 mmol), EDC (1.58 g, 8.26 mmol) and HOAt (1.23 g, 8.26 mmol) in DMF (10 mL) was stirred at 22° C. for 2 hours. The reaction mixture was diluted with aqueous saturated NaHCO3 (30 mL), and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×30 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 5-50% EtOAc/hexane, to give the title product (1.42 g, 81%). LRMS (ESI) m/z 256.3 [(M+H)+; calcd for C14H26NO3: 256.2]. extracted with EtOAc (3×50 mL) The combined organic layers were washed with water (3×30 mL), brine (20 mL) dried over Na2SO4 filtered concentrated The residue was chromatographed on silica gel eluting with 5-50% EtOAc/hexane

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

Procedure: A solution of L-t-leucine methyl ester (1.00 g, 6.89 mmol), 6-heptenoic acid (1.06 g, 8.26 mmol), EDC (1.58 g, 8.26 mmol) and HOAt (1.23 g, 8.26 mmol) in DMF (10 mL) was stirred at 22° C. for 2 hours. The reaction mixture was diluted with aqueous saturated NaHCO3 (30 mL), and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×30 mL), brine (20 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 5-50% EtOAc/hexane, to give the title product (1.42 g, 81%). LRMS (ESI) m/z 256.3 [(M+H)+; calcd for C14H26NO3: 256.2]. extracted with EtOAc (3×50 mL) The combined organic layers were washed with water (3×30 mL), brine (20 mL) dried over Na2SO4 filtered concentrated The residue was chromatographed on silica gel eluting with 5-50% EtOAc/hexane