Formic Acid → Acetic-formic anhydride

Participants

Reaction Steps

Formic acetic anhydride was prepared by adding 96% formic acid (1.24 ml, 32.2 mmol) to acetic anhydride (1.52 ml, 16.1 mmol) and stirring for 1 hour. (Ref: Org. Process Research & Development, 2000, 4, p. 567-570). Formic acetic anhydride (0.16 ml, 0.87 mmol) was added to a solution of 1,1-dimethylethyl[2-amino-4-({4-[(2,3-dihydro-1H-inden-2-yl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]phenyl}oxy)phenyl]carbamate (430 mg, 0.79 mmol) in 20 mL of tetrahydrofuran. The reaction mixture was stirred for 30 minutes then quenched with 2 mL of 1N NaOH and stirred vigorously. The reaction was passed through a Varian Chem Elute™ 1010 tube that was pretreated for five minutes with 2 mL of 1N NaOH. The tube was eluted with ethyl acetate. The eluent was dried over MgSO4 and concentrated to give 1,1-dimethylethyl 2,3-dihydro-1H-inden-2-yl[(4-{[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-(formylamino)phenyl]oxy}phenyl)methyl]carbamate. (M-1) 572.0, 2.93 min (LC/MS method B)

Provenance & Evidence