تفاعل #534174

معادلة التفاعل

HATU

Boc-N(Me)Ala-OH

58

{2-[4-(2-Amino-3,3-dimethyl-butyryl)-3-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

NMM

→

59

المردود 75.4%

(1-{1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

المردود 75.4%

المذيبات

EtOAc

NMP

NMP

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed successively with 1M HCl, saturated NaHCO3
2. 2
   تجفيفdried over anhydrous Na2SO4
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىPurification by reverse phase HPLC (2″ Dynamax® C18, 10-70% ACN in H2O with 0.1% HOAc over 30 min)

الإجراء التجريبي

A solution of Boc-N(Me)Ala-OH (152 mg, 0.74 mmol) in NMP (3 mL) was cooled to 0° C. and treated with HATU (313 mg, 0.83 mmol) followed by NMM (0.15 mL). After 10 min, 58 (450 mg) in NMP (2 mL) was added. The reaction mixture was allowed to warm to ambient temperature overnight. The solution was diluted with EtOAc, washed successively with 1M HCl, saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated. Purification by reverse phase HPLC (2″ Dynamax® C18, 10-70% ACN in H2O with 0.1% HOAc over 30 min) afforded 59 as a white solid (430 mg). Mass spectrum, m/z [771.3] (M+H)+.

المصدر