반응 #1821

ord-61e90dfc436e46c68b3d763ba8118cbb

반응 방정식

Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
material
Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
2' Deoxycytidine
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
crystalline product
수율 98.2%
CC(=O)Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
N4 -Acetyl-2'Deoxycytidine
수율 98.2%

반응물

Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
material
Nc1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)n1
2' Deoxycytidine
CC(=O)OC(C)=O
acetic anhydride

시약

없음

용매

CN(C)C=O
N,N-dimethylformamide

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타DMF was removed under reduced pressure
  2. 2
    workup.ADDITIONthe resulting residue was treated with the excess of 100 ml dimethyl ether

실험 절차

To 61.29 g (270 mmol) of the material of Example I dissolved in 1300 ml of anhydrous N,N-dimethylformamide ("DMF") (Aldrich; Cat. No. 22, 70506), was added 28 ml (296 mmol) of acetic anhydride (Aldrich; Cat. No. 11,004-3), and the resulting mixture was stirred at room temperature for 20 hrs. DMF was removed under reduced pressure, and the resulting residue was treated with the excess of 100 ml dimethyl ether; 71.4 g (98% yield) of a crystalline product was obtained and collected by filtration, washed thoroughly with dimethyl ether, and dried over P2O5 for 3 hrs. This product had a melting point of 150°-170° C.; the published melting point for this product 154°-176° C.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05726301uspto-grants-1998_03