1-(chloromethyl)-4-(2-methylpropyl)benzene

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

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

Procedure: A solution of ethyl 4-[3-[3,5-bis[tertbutoxycarbonylamino)benzoyl]indol-1-yl]butyrate (300 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 54 mg) in N,N-dimethylformamide (5 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and a solution of 4-isobutylbenzyl chloride (388 mg) in N,N-dimethylformamide (5 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and poured into a mixture of 0.1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous solution of sodium bicarbonate and brine in successively. After dryness over magnesium sulfate and evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3,5-bis[N-(4-isobutylbenzyl)-N-tert-butoxycarbonyl- amino]benzoyl]indol-1-yl]butyrate (155 mg) as an oil. The reaction mixture was stirred at 0° C. for 3 hours The organic layer was separated washed with water, aqueous solution of sodium bicarbonate and brine in successively After dryness over magnesium sulfate and evaporation of the solvent the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4)

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

Procedure: A solution of ethyl 4-[3-[3,5-bis[tertbutoxycarbonylamino)benzoyl]indol-1-yl]butyrate (300 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 54 mg) in N,N-dimethylformamide (5 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and a solution of 4-isobutylbenzyl chloride (388 mg) in N,N-dimethylformamide (5 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and poured into a mixture of 0.1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous solution of sodium bicarbonate and brine in successively. After dryness over magnesium sulfate and evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3,5-bis[N-(4-isobutylbenzyl)-N-tert-butoxycarbonyl- amino]benzoyl]indol-1-yl]butyrate (155 mg) as an oil. The reaction mixture was stirred at 0° C. for 3 hours The organic layer was separated washed with water, aqueous solution of sodium bicarbonate and brine in successively After dryness over magnesium sulfate and evaporation of the solvent the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4)

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

Procedure: A solution of ethyl 4-[3-[3,5-bis(tertbutoxycarbonylamino)benzoyl]indol-1-yl]butyrate (300 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 54 mg) in N,N-dimethylformamide (5 ml ) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and a solution of 4-isobutylbenzyl chloride (38.8 mg) in N,N-dimethylformamide (5 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and poured into a mixture of 0.1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous solution of sodium bicarbonate and brine in successively. After dryness over magnesium sulfate and evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3,5-bis[N-(4-isobutylbenzyl )-N-tert-butoxycarbonylamino] benzoyl]indol-1-yl]butyrate (155 mg) as an oil. The reaction mixture was stirred at 0° C. for 3 hours The organic layer was separated washed with water, aqueous solution of sodium bicarbonate and brine in successively After dryness over magnesium sulfate and evaporation of the solvent the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4)

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

Procedure: A solution of ethyl 4-[3-[3,5-bis(tertbutoxycarbonylamino)benzoyl]indol-1-yl]butyrate (300 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 54 mg) in N,N-dimethylformamide (5 ml ) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and a solution of 4-isobutylbenzyl chloride (38.8 mg) in N,N-dimethylformamide (5 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and poured into a mixture of 0.1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous solution of sodium bicarbonate and brine in successively. After dryness over magnesium sulfate and evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3,5-bis[N-(4-isobutylbenzyl )-N-tert-butoxycarbonylamino] benzoyl]indol-1-yl]butyrate (155 mg) as an oil. The reaction mixture was stirred at 0° C. for 3 hours The organic layer was separated washed with water, aqueous solution of sodium bicarbonate and brine in successively After dryness over magnesium sulfate and evaporation of the solvent the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4)

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

Procedure: A solution of ethyl 4-[3-[3,5-bis[tertbutoxycarbonylamino)benzoyl]indol-1-yl]butyrate (300 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 54 mg) in N,N-dimethylformamide (5 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and a solution of 4-isobutylbenzyl chloride (388 mg) in N,N-dimethylformamide (5 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and poured into a mixture of 0.1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous solution of sodium bicarbonate and brine in successively. After dryness over magnesium sulfate and evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3,5-bis[N-(4-isobutylbenzyl)-N-tert-butoxycarbonyl- amino]benzoyl]indol-1-yl]butyrate (155 mg) as an oil. The reaction mixture was stirred at 0° C. for 3 hours The organic layer was separated washed with water, aqueous solution of sodium bicarbonate and brine in successively After dryness over magnesium sulfate and evaporation of the solvent the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4)

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

Procedure: 3-chloro-4-(4'-isobutylbenzyloxy) phenylacetic acid was prepared in accordance with the procedure designated (f) above by reacting 4-isobutylbenzyl chloride and methyl 3-chloro-4-hydroxyphenylacetate. The resultant product evidenced a melting point of 97°-99° C. (methanol-water 4:1), the yield being 61%.

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

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

Procedure: 3-chloro-4-(4'-isobutylbenzyloxy) phenylacetic acid was prepared in accordance with the procedure designated (f) above by reacting 4-isobutylbenzyl chloride and methyl 3-chloro-4-hydroxyphenylacetate. The resultant product evidenced a melting point of 97°-99° C. (methanol-water 4:1), the yield being 61%.

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

Procedure: 527 g of 4-isobutylbenzyl chloride, 153 g of sodium cyanide and 720 ml of dimethylsulfoxide are agitated for 6 hours at 40° C. The mixture is cooled and then diluted with water. An oily layer separates and is extracted with ether. The ether solution is subjected to fractionation and yields 367 g of 4-isobutylphenyl acetonitrile. The mixture is cooled An oily layer separates and is extracted with ether

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

Procedure: A solution of ethyl 4-[3-[3,5-bis(tertbutoxycarbonylamino)benzoyl]indol-1-yl]butyrate (300 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 54 mg) in N,N-dimethylformamide (5 ml ) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and a solution of 4-isobutylbenzyl chloride (38.8 mg) in N,N-dimethylformamide (5 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and poured into a mixture of 0.1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous solution of sodium bicarbonate and brine in successively. After dryness over magnesium sulfate and evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3,5-bis[N-(4-isobutylbenzyl )-N-tert-butoxycarbonylamino] benzoyl]indol-1-yl]butyrate (155 mg) as an oil. The reaction mixture was stirred at 0° C. for 3 hours The organic layer was separated washed with water, aqueous solution of sodium bicarbonate and brine in successively After dryness over magnesium sulfate and evaporation of the solvent the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4)

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

Procedure: A solution of ethyl 4-[3-[3,5-bis[tertbutoxycarbonylamino)benzoyl]indol-1-yl]butyrate (300 mg) in N,N-dimethylformamide (5 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 54 mg) in N,N-dimethylformamide (5 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, and a solution of 4-isobutylbenzyl chloride (388 mg) in N,N-dimethylformamide (5 ml) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, and poured into a mixture of 0.1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water, aqueous solution of sodium bicarbonate and brine in successively. After dryness over magnesium sulfate and evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-[3,5-bis[N-(4-isobutylbenzyl)-N-tert-butoxycarbonyl- amino]benzoyl]indol-1-yl]butyrate (155 mg) as an oil. The reaction mixture was stirred at 0° C. for 3 hours The organic layer was separated washed with water, aqueous solution of sodium bicarbonate and brine in successively After dryness over magnesium sulfate and evaporation of the solvent the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4)