Bromine → 115249-86-0

HRID 1492882Notes

Reaction equation

HRID 1492882 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:3]1.[Br:17]Br>C(O)(=O)C>[Br:17][C:15]1[C:13](=[O:14])[NH:12][C:10](=[O:11])[N:9]([C@@H:4]2[O:5][C@H:6]([CH2:7][OH:8])[C@@H:2]([F:1])[CH2:3]2)[CH:16]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 1624502',3'-Dideoxy-3'-fluorouridine

Product 1

HCID 451481115249-86-0Yield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

The 5'-O-toluoyl derivative of 1-(2,3-dideoxy-3-fluoro-β-D-erythropentofuranosyl)uracil, prepared as described in Example 1, (200 mg, 0.574 mmol), glacial acetic acid (5 ml) and bromine (0.08 ml of an 8M solution in glacial acetic acid, 0.64 mequiv.) were stirred at 25° for 18 hours. The solution was evaporated to a glass which was treated with sodium methoxide and methanol as described in Example 1. Product was eluted from a silica gel column with 5% MeOH-CH2Cl2 as white crystals (135 mg). Recrystallization from EtOH gave title compound as white crystals (115 mg, 64% overall yield); m.p. 193.5°-194° dec.; Anal Calcd for C9H10BrFN2O4 : C, 34.97; H, 3.26; N, 9.06; Br, 25.85; F, 6.15. Found: C, 35.07; H, 3.31; N, 9.00; Br, 25.78; F, 6.04; UV λ max (H2O): 277 nM; structure further confirmed by 'H-NMR and mass spectrum.

Workup

  1. customThe solution was evaporated to a glass which
  2. additionwas treated with sodium methoxide and methanol
  3. washProduct was eluted from a silica gel column with 5% MeOH-CH2Cl2 as white crystals (135 mg)
  4. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-10e8854bf7214c02879ffa3e0ba83e60
Source dataset
uspto-grants-1994_12
Patent number
US05376644

Reaction notes

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