Acetic Anhydride → HCID 18648378, compound

HRID 1614691Notes

Reaction equation

HRID 1614691 reaction equation
[C:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:10]([F:15])[CH2:9]1)#[CH:2].[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([O:13][CH2:12][C@H:11]1[O:14][C@@H:8]([N:7]2[CH:16]=[C:3]([C:1]#[CH:2])[C:4](=[O:18])[NH:5][C:6]2=[O:17])[CH2:9][C@@H:10]1[F:15])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 10445008HCID 10445008, compound

Product 1

HCID 18648378HCID 18648378, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2',3'-dideoxy-5-ethynyl-3'-fluorouridine (1.106 g 0.4 mmol) in dry pyridine (5 ml) at 0° C. was added acetic anhydride (0.05 ml, 0.48 mmol) and stirring maintained at 0° C. for 1.5 hours. After stirring at room temperature for 24 hours, a further aliquot of acetic anhydride (0.02 ml, 0.2 mmol) was added and the mixture stirred at room temperature for 3 hours. After quenching with methanol (1 ml) the solvent was removed by evaporation under reduced pressure and co-evaporated with portions of ethanol (2×30 ml). The residue was recrystallised from ethanol to give a white crystalline solid.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. stirringthe mixture stirred at room temperature for 3 hours
  3. customAfter quenching with methanol (1 ml) the solvent
  4. customwas removed by evaporation under reduced pressure and co-evaporated with portions of ethanol (2×30 ml)
  5. customThe residue was recrystallised from ethanol
  6. customto give a white crystalline solid

Sources & evidence

ORD record
ord-4dfa2f2d30dd4f069af5f4326816e70c
Source dataset
uspto-grants-1993_03
Patent number
US05198539

Reaction notes

Loading…