تفاعل #417939

ord-f98975836de142908572b859df61903d

معادلة التفاعل

C[C@H](NC(=O)OC(C)(C)C)C(=O)O
t-Boc-Ala
C(=NC1CCCCC1)=NC1CCCCC1
N,N′-Dicyclohexylcarbodiimide
O=C(NC1CCCCC1)NC1CCCCC1
Dicyclohexylurea

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

t-Boc-Ala (4.16 gr, 22 mmol) was dissolved in 11 ml dioxane. N,N′-Dicyclohexylcarbodiimide (DCC) (11 mmol in 11 ml 1 M DMF) was then added and the reaction was carried out for 3 hours at 25° C. under stirring. Dicyclohexylurea (DCU) formed was removed by centrifugation. The symmetrical anhydride product thus obtained (t-Boc-Ala-anhydride) was reacted overnight under stirring with 2-aminofluorene (0.925 g, 11 mmol) in 30 ml dioxane-water (1:1, v:v) containing 11 mmol of NaHCO3. The white solid formed was collected and dried under P2O5 in vacuum for 24 hours. Intermediate a was obtained in 60% yield (1.31 g, 3.34 mmol). It migrated on TLC (dichloromethane) with Rt=0.17. Mass-spectroscopy revealed a mass of 352.45 Da (calculated mass=352.2 Da).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08877709B2uspto-grants-2014_11