Acetic Anhydride → Thymidine, 3'-deoxy-3'-fluoro-, 5'-acetate

HRID 465303

Reaction equation

HRID 465303 reaction equation
[CH3:1][C:2]([O:4][C:5]([CH3:7])=[O:6])=O.[F:8][C@@H:9]1[C@@H](CO)[O:12][C@@H:11]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:10]1>N1C=CC=CC=1>[C:5]([O:4][CH2:2][C@H:1]1[O:12][C@@H:11]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:10][C@@H:9]1[F:8])(=[O:6])[CH3:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 330393'-Fluorothymidine

Product 1

HCID 453016Thymidine, 3'-deoxy-3'-fluoro-, 5'-acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

56 mMol acetanhydride is added at 0° C. to a solution of 50 mMol 3'-deoxy-3'-fluorothymidine in 50 ml pyridine. The reaction solution stands overnight at room temperature and is subsequently poured into ice water. The aqueous phase is decanted. The oily product is purified in a chromatographic column on silica gel with chloroform eluent. The fractions obtained from the product are isolated as a solid material which is recrystallized from ethanol. M.P.97°-98° C.

Workup

  1. customThe aqueous phase is decanted
  2. customThe oily product is purified in a chromatographic column on silica gel with chloroform eluent
  3. customThe fractions obtained from the product
  4. customare isolated as a solid material which
  5. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-6552d41b562c4810be538d9a4db56c15
Source dataset
uspto-grants-1992_10
Patent number
US05153180

Linked notes

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