Pyridine → N-Acetyl-2'-deoxy-2'-fluorocytidine

HRID 2229752Notes

Reaction equation

HRID 2229752 reaction equation
Cl.[F:2][C@@H:3]1[C@H:7]([OH:8])[C@@H:6]([CH2:9][OH:10])[O:5][C@H:4]1[N:11]1[CH:18]=[CH:17][C:15]([NH2:16])=[N:14][C:12]1=[O:13].N1C=CC=CC=1.C(#N)C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C(N(CC)CC)C.CN(C=O)C>[C:28]([NH:16][C:15]1[CH:17]=[CH:18][N:11]([C@@H:4]2[O:5][C@H:6]([CH2:9][OH:10])[C@@H:7]([OH:8])[C@H:3]2[F:2])[C:12](=[O:13])[N:14]=1)(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 69101485HCID 69101485, compound

Product 1

HCID 22094552N-Acetyl-2'-deoxy-2'-fluorocytidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1 g (about 4 mmol) of 2′-fluoro-2′-deoxycytidine hydrochloride is coevaporated with 20 ml of abs. pyridine twice and twice with 10 ml of abs. acetonitrile each time in a 100 ml Schlenk flask. The dried nucleosidic material is suspended in 40 ml of abs. DMF, and 0.6 ml (about 4.4 mmol) of acetic anhydride is added. Over the course of one day 0.5 ml (4.4 mmol) of abs. triethylamine is added dropwise to the mixture. The solvent is subsequently stripped off under oil pump vacuum. The crude product is washed with 50 ml of diethyl ether and subsequently dried. Purification was by column chromatography (silica gel 60 H, column 4×10 cm, mobile phase methylene chloride with 0.1% pyridine, gradient methanol); the product is eluted at 8% methanol.

Workup

  1. customOver the course of one day 0.5 ml (4.4 mmol) of abs
  2. washThe crude product is washed with 50 ml of diethyl ether
  3. customsubsequently dried
  4. customPurification
  5. washthe product is eluted at 8% methanol

Sources & evidence

ORD record
ord-3eca3453ee844f8985a62fb061026e4e
Source dataset
uspto-grants-2002_07
Patent number
US06420546B1

Reaction notes

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