Benzoyl chloride → 1-(2'-O-Benzoyl-beta-D-ribopyranosyl)-5-(2-phtalimidoethyl)uracil

HRID 860843Notes

Reaction equation

HRID 860843 reaction equation
[C:1]1(=[O:30])[N:5]([CH2:6][CH2:7][C:8]2[C:9](=[O:24])[NH:10][C:11](=[O:23])[N:12]([C@@H:14]3[O:22][CH2:21][C@@H:19]([OH:20])[C@@H:17]([OH:18])[C@H:15]3[OH:16])[CH:13]=2)[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[NH4+]>N1C=CC=CC=1.ClCCl>[C:31]([O:16][C@@H:15]1[C@H:17]([OH:18])[C@H:19]([OH:20])[CH2:21][O:22][C@H:14]1[N:12]1[CH:13]=[C:8]([CH2:7][CH2:6][N:5]2[C:4](=[O:25])[C:3]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]3[C:1]2=[O:30])[C:9](=[O:24])[NH:10][C:11]1=[O:23])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 25517Ammonium ChlorideHCID 154080305-(2-Phtalimidoethyl)-1-(beta-D-ribopyranosyl)uracil

Product 1

HCID 154080311-(2'-O-Benzoyl-beta-D-ribopyranosyl)-5-(2-phtalimidoethyl)uracilYield 60,597.301%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

10.6 g (0.025 mmol) of 5-(2-phtalimidoethyl)-1-(β-D-ribopyranosyl)uracil were dissolved in 20 ml of pyridine in a heated and argon-flushed 1 l four-necked flask and mixed with 200 ml of dichloromethane. The mixture was cooled to −70° C., 3.82 ml (0.033 mmol) of benzoyl chloride in 5 ml of pyridine and 20 ml of dichloromethane were slowly added dropwise with cooling and the mixture was stirred at −70° C. for 35 min. The reaction mixture was poured onto 600 ml of cooled ammonium chloride solution and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water, dried and concentrated to dryness in vacuo. Chromatography on silica gel (ethyl acetate/heptane 1:1) yielded 7.9 g (60%) of 1-(2′-O-benzoyl-β-D-ribopyranosyl)-5-(2-phtalimidoethyl)uracil.

Workup

  1. temperaturea heated
  2. customargon-flushed 1 l four-necked flask
  3. additionmixed with 200 ml of dichloromethane
  4. temperaturewith cooling
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. washThe combined organic phases were washed with water
  7. customdried
  8. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-5a9a8a470c4f4e4682d84ef7255904f2
Source dataset
uspto-grants-2006_12
Patent number
US07153955B2

Reaction notes

Loading…