Pivaloyl chloride → HCID 18648374, compound

HRID 466741Notes

Reaction equation

HRID 466741 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:14][C@H:11]([CH2:12][OH:13])[C@@H:10]([F:15])[CH2:9]1)#[CH:2].[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22]>N1C=CC=CC=1>[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:14][C@H:11]([CH2:12][O:13][C:21](=[O:22])[C:20]([CH3:25])([CH3:24])[CH3:19])[C@@H:10]([F:15])[CH2:9]1)#[CH:2]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 10445008HCID 10445008, compound

Product 1

HCID 18648374HCID 18648374, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2',3'-dideoxy-5-ethynyl-3'-fluorouridine (0.106 g 0.4 mmol) in dry pyridine (5 ml) at 0° C. was added trimethylacetyl chloride (0.06 ml, 0.48 mmol) and stirring continued at 0° C. for 1.5 hours. After stirring at room temperature for 24 hours, a further aliquot of the acid chloride (0.03 ml, 0.24 mmol) was added and stirring maintained for a further 3 hours. After quenching with methanol (3 ml), the solvent was removed by evaporation under reduced pressure and co-evaporated with several portions of ethanol (2×30 ml) and the resulting oil was chromatrographed on a silica gel column eluting with 5% MeOH/CH2Cl2. The appropriate fractions were combined and evaporated to dryness and the residue was recrystallised twice from ethanol to give the chromatographically pure title product.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. stirringstirring
  3. temperaturemaintained for a further 3 hours
  4. customAfter quenching with methanol (3 ml)
  5. customthe solvent was removed by evaporation under reduced pressure and co-evaporated with several portions of ethanol (2×30 ml)
  6. washeluting with 5% MeOH/CH2Cl2
  7. customevaporated to dryness
  8. customthe residue was recrystallised twice from ethanol

Sources & evidence

ORD record
ord-3aa23e1d64414b78a9557a22d1cd281a
Source dataset
uspto-grants-1992_10
Patent number
US05157114

Reaction notes

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