tert-butyl chloromethyl carbonate

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

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

Procedure: 0.22 mL Et3N was added to a mixture of 0.700 g 4-ethyl-2-propyl-1-[[2'-(N-triphenylmethyl(tetrazol-5-yl))biphenyl-4-yl]methyl]imidazole-5-carboxylate, 0.26 g t-butyl chloromethyl carbonate and 0.59 g n-Bu4NI in 5 mL dry THF under Ar. The reaction was stirred 6 days at room temperature and then concentrated on a rotary evaporator. The residue was partitioned between H2O and CH2Cl2, and the organic extracts dried with MgSO4. Flash chromatography using 1:1 EtOAc/petroleum ether(bp 40°-60° C.) gave 0.40 g of the title compound. concentrated on a rotary evaporator The residue was partitioned between H2O and CH2Cl2 the organic extracts dried with MgSO4

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

Procedure: 0.62 mL pyridine was added dropwise to a solution of 0.77 g chloromethyl chloroformate and 1.32 mL t-BuOH in 60 mL CH2Cl2 cooled in an ice bath under an Ar atmosphere. The reaction was stirred 2 hours at 0° C. then transferred to a separatory funnel. The reaction was washed twice with H2O, once with 10% CuSO4, once with brine and dried with MgSO4. Suction filtration and evaporation provided 0.55 g of desired product which was used without purification. cooled in an ice bath under an Ar atmosphere then transferred to a separatory funnel The reaction was washed twice with H2O, once with 10% CuSO4, once with brine dried with MgSO4 Suction filtration and evaporation

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

Procedure: 0.62 mL pyridine was added dropwise to a solution of 0.77 g chloromethyl chloroformate and 1.32 mL t-BuOH in 60 mL CH2Cl2 cooled in an ice bath under an Ar atmosphere. The reaction was stirred 2 hours at 0° C. then transferred to a separatory funnel. The reaction was washed twice with H2O, once with 10% CuSO4, once with brine and dried with MgSO4. Suction filtration and evaporation provided 0.55 g of desired product which was used without purification. cooled in an ice bath under an Ar atmosphere then transferred to a separatory funnel The reaction was washed twice with H2O, once with 10% CuSO4, once with brine dried with MgSO4 Suction filtration and evaporation

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

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

Procedure: 0.22 mL Et3N was added to a mixture of 0.700 g 4-ethyl-2-propyl-1-[[2'-(N-triphenylmethyl(tetrazol-5-yl))biphenyl-4-yl]methyl]imidazole-5-carboxylate, 0.26 g t-butyl chloromethyl carbonate and 0.59 g n-Bu4NI in 5 mL dry THF under Ar. The reaction was stirred 6 days at room temperature and then concentrated on a rotary evaporator. The residue was partitioned between H2O and CH2Cl2, and the organic extracts dried with MgSO4. Flash chromatography using 1:1 EtOAc/petroleum ether(bp 40°-60° C.) gave 0.40 g of the title compound. concentrated on a rotary evaporator The residue was partitioned between H2O and CH2Cl2 the organic extracts dried with MgSO4

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

Procedure: 0.62 mL pyridine was added dropwise to a solution of 0.77 g chloromethyl chloroformate and 1.32 mL t-BuOH in 60 mL CH2Cl2 cooled in an ice bath under an Ar atmosphere. The reaction was stirred 2 hours at 0° C. then transferred to a separatory funnel. The reaction was washed twice with H2O, once with 10% CuSO4, once with brine and dried with MgSO4. Suction filtration and evaporation provided 0.55 g of desired product which was used without purification. cooled in an ice bath under an Ar atmosphere then transferred to a separatory funnel The reaction was washed twice with H2O, once with 10% CuSO4, once with brine dried with MgSO4 Suction filtration and evaporation