تفاعل #315275

معادلة التفاعل

N-(3-hydroxypropyl)-carbamic acid tert-butyl ester

triphosgene

DIEA

(2R)-2-amino-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)propan-1-one TFA salt

DIEA

N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl}piperazinyl)-2-oxoethyl](3-aminopropoxy)carboxamide

→

TFA

title compound

N-[(1R)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](3-aminopropoxy)carboxamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe Boc protecting group was removed
2. 2
   workup.ADDITIONby treating with a soln of 50% TFA in CH2Cl2 (2 mL) for 2 h
3. 3
   أخرىThe crude product was purified by preparative TLC (60% hexane, 38% CH2Cl2 and 2% 2N NH3 in MeOH)

الإجراء التجريبي

Following the procedure of Example 51, N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl}piperazinyl)-2-oxoethyl](3-aminopropoxy)carboxamide, was prepared from N-(3-hydroxypropyl)-carbamic acid tert-butyl ester (Aldrich) (40 mg, 0.230 mmol), triphosgene (Avocado) (30 mg, 0.1 mmol), DIEA (0.040 mL, 0.230 mmol), (2R)-2-amino-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)propan-1-one TFA salt (200 mg, 0.36 mmol), and more DIEA (0.34 mL, 2.0 mmol). The Boc protecting group was removed by treating with a soln of 50% TFA in CH2Cl2 (2 mL) for 2 h. The crude product was purified by preparative TLC (60% hexane, 38% CH2Cl2 and 2% 2N NH3 in MeOH) and then by preparative HPLC (TFA buffer) to afford the title compound (TFA salt) as a white solid (10 mg). MS (ESI, pos. ion) m/z: 538 (M+H); MS (ESI, neg. ion) m/z: 536 (M−H). Calc'd for C24H32ClN5O5S: 537.18.

المصدر