HRID2043792

反应详情

EQUATION

反应方程式

HRID 2043792 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

2

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

1-O-Acetyl-3,5-di-O-(4-chloro-benzoyl)-2-deoxy-D-ribofuranose (3.603 Kg, 7.68 mol), 2-[(trimethylsilyl)amino]-4-[(trimethylsilyl)oxy]-s-triazine (1.970 Kg, 7.68 mol) and dichloromethane (71.6 Kg) were charged to a suitable reactor. The mixture was cooled to 0° C. TMSOTf (1.791 Kg, 8.06 mol) was added to the solution at 0° C. and stirred for 5 hours. 2M methyl amine in methanol solution (about 3.95 Kg) was then added to the mixture at 0° C. and stirred for 45 mins. The mixture was diluted with dichloromethane (71.6 Kg) and washed with saturated sodium bicarbonate solution (39.8 Kg) at 25° C. The organic layer was dried using molecule sieves (36 Kg). The molecule sieves were filtered and rinsed with dichloromethane (60.1 Kg). The organic layer was evaporated to dryness at 35° C. The solid was milled and vacuum dried at 45° C. to obtain 2.99 Kg (5.92 mol) of 4-amino-1-[3,5-di-O-(4-chloro-benzoyl)-2-deoxy-β-D-ribofuranosyl]-1H-[1,3,5]triazin-2-one (compound Ib) in 52% HPLC purity (40% yield based on 1-O-acetyl-3,5-di-O-(4-chloro-benzoyl)-2-deoxy-D-ribofuranose) and 4-amino-1-[3,5-di-O-(4-chloro-benzoyl)-2-deoxy-α-D-ribofuranosyl]-1H-[1,3,5]triazin-2-one (compound IVa) mixture in 27% HPLC purity. That α-anomer to β-anomer ratio was 1.0:1.91.

WORKUP

后处理

  1. stirringstirred for 45 mins
  2. washwashed with saturated sodium bicarbonate solution (39.8 Kg) at 25° C
  3. customThe organic layer was dried
  4. filtrationThe molecule sieves were filtered
  5. washrinsed with dichloromethane (60.1 Kg)
  6. customThe organic layer was evaporated to dryness at 35° C
  7. customThe solid was milled
  8. customvacuum dried at 45° C.