تفاعل #1333183

ord-6cf77043b7d4418ba42799bce880ee95

معادلة التفاعل

CC(C)(C)OC(=O)CC[C@H](N)C(=O)Nc1cccc(COc2ccc3[nH]c(C(N)=O)cc3c2)c1
2-Carbamoyl-5-[3-(O-tert-butyl-α-glutamylamino)benzyloxy]-1H-indole
Cl
HCl
→
NC(=O)c1cc2cc(OCc3cccc(NC(=O)[C@@H](N)CCC(=O)O)c3)ccc2[nH]1
2-carbamoyl-5-[3-(α-glutamylamino)benzyloxy]-1H-indole
المردود 51.0%

المتفاعلات

CC(C)(C)OC(=O)CC[C@H](N)C(=O)Nc1cccc(COc2ccc3[nH]c(C(N)=O)cc3c2)c1
2-Carbamoyl-5-[3-(O-tert-butyl-α-glutamylamino)benzyloxy]-1H-indole
Cl
HCl

الكواشف

لا شيء

المذيبات

ClCCl
CH2Cl2
C1COCCO1
dioxan

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىevaporated
  2. 2
    أخرىthe residue was purified on OASIS resin
  3. 3
    غسيلeluting with H2O/CH3CN 80/20

الإجراء التجريبي

2-Carbamoyl-5-[3-(O-tert-butyl-α-glutamylamino)benzyloxy]-1H-indole (0.29 g; 0.62 mmol) in solution in CH2Cl2 (2 ml) was treated under argon with HCl (2N) in dioxan (4 ml). The mixture was stirred for one hour, evaporated and the residue was purified on OASIS resin, eluting with H2O/CH3CN 80/20 to give 2-carbamoyl-5-[3-(α-glutamylamino)benzyloxy]-1H-indole.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07125906B2uspto-grants-2006_10