HCID 57370091, compound → Cytidine, 5′-deoxy-5-fluoro-5′-iodo-

HRID 1834896Notes

Reaction equation

HRID 1834896 reaction equation
CC1(C)[O:9][CH:8]2[C@H:4]([C@@H:5]([CH2:19][I:20])[O:6][C@H:7]2[N:10]2[C:15](=[O:16])[N:14]=[C:13]([NH2:17])[C:12]([F:18])=[CH:11]2)[O:3]1>FC(F)(F)C(O)=O.O>[I:20][CH2:19][C@H:5]1[O:6][C@@H:7]([N:10]2[CH:11]=[C:12]([F:18])[C:13]([NH2:17])=[N:14][C:15]2=[O:16])[C@H:8]([OH:9])[C@@H:4]1[OH:3]

Participants

3

Reactant 1

HCID 57370091HCID 57370091, compound

Product 1

HCID 54037794Cytidine, 5′-deoxy-5-fluoro-5′-iodo-

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

A solution of 5'-deoxy-5'-iodo-2',3'-O-isopropylidene-5-fluorocytidine (20 g) in trifluoroacetic acid/water (9:1, 100 ml) was stored at room temperature for 70 min. The solution was evaporated to dryness, co-evaporated with ethanol (2 × 200 ml) and dissolved in ethyl acetate (200 ml). Triethylamine was added to neutrality, and after storage overnight the crystals were collected and dried. Yield = 16.8 g (93%).

Workup

  1. customThe solution was evaporated to dryness, co-evaporated with ethanol (2 × 200 ml)
  2. dissolutiondissolved in ethyl acetate (200 ml)
  3. additionTriethylamine was added to neutrality
  4. customafter storage overnight the crystals were collected
  5. customdried

Sources & evidence

ORD record
ord-b1badf18ddc446f2b3a1c9bae923bd8d
Source dataset
uspto-grants-1978_01
Patent number
US04071680

Reaction notes

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