N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[t-butyloxycarbonylaminosulfonyl]-amino-acetic acid ethyl ester → N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester

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Reaction Steps

The title M compound, N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[t-butyloxycarbonylaminosulfonyl]-amino-acetic acid ethyl ester (124 mg, 0.19 mmol) is dissolved in CH2Cl2-TFA-triethylsilane (2.5:7:0.5, 1.5 mL) and the solution is stirred at RT for 1 h and evaporated. The residue is dissolved in EtOAc and the solution is washed twice with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and evaporated to give N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester as a foam: [M+1]+=553.

Provenance & Evidence