Benzoyl chloride → HCID 22842024, compound

HRID 1089664Notes

Reaction equation

HRID 1089664 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:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1)#[CH:2].C(N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C.Cl[Si](C)(C)C>[C:26]([N:5]1[C:4](=[O:18])[C:3]([C:1]#[CH:2])=[CH:16][N:7]([C@@H:8]2[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]2)[C:6]1=[O:17])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 4721725-Ethynyl-2′-deoxyuridine

Product 1

HCID 22842024HCID 22842024, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6397ChlorotrimethylsilaneSolvent

Procedure

To a stirred suspension of 2'deoxy-5-ethynyluridine (J. Med. Chem., 26(5), 661-6, (1983)) (0.3 g, 1.19 mmoles) in dry acetonitrile (8 ml) and chlorotrimethylsilane (0.5 ml) was added, with ice cooling, triethylamine (0.85 ml, 6.1 mmoles) and the whole was stirred at room temperature for 2 hrs. Benzoylchloride (0.18 ml, 1.54 mmoles) was then added and the mixture stirred for a further 1.5 hrs and filtered. The filtrate was concentrated, the residue dissolved in ethanol (10 ml) and glacial acetic acid (0.4 g) was added. After stirring for 0.5 hr, the solvents were evaporated and the residue purified by column chromatography on silica gel eluting with methylene chloride/methanol (19:1) to give the title compound 0.2 g (47% yield) melting at 156°-7° C.

Workup

  1. stirringthe mixture stirred for a further 1.5 hrs
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue dissolved in ethanol (10 ml)
  5. additionglacial acetic acid (0.4 g) was added
  6. stirringAfter stirring for 0.5 hr
  7. customthe solvents were evaporated
  8. customthe residue purified by column chromatography on silica gel eluting with methylene chloride/methanol (19:1)

Sources & evidence

ORD record
ord-46b57773c76444f6b7527b3347017afa
Source dataset
uspto-grants-1992_01
Patent number
US05079235

Reaction notes

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