Dichloromethane → HCID 18634663, compound

HRID 1606891Notes

Reaction equation

HRID 1606891 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:8]([C:10]1[C:11](=[O:25])[NH:12][C:13](=[O:24])[N:14]([CH:23]=1)[C@@H:15]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[CH2:16]1)#[CH:9].C(Cl)Cl>N1C=CC=CC=1.C(Cl)Cl.CO>[C:1]([O:18][C@@H:17]1[C@@H:19]([CH2:20][O:21][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[O:22][C@@H:15]([N:14]2[CH:23]=[C:10]([C:8]#[CH:9])[C:11](=[O:25])[NH:12][C:13]2=[O:24])[CH2:16]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 62493Pivaloyl chlorideHCID 4721725-Ethynyl-2′-deoxyuridine

Product 1

HCID 18634663HCID 18634663, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Pivaloyl chloride (0.3 ml, 2.56 mmoles) was added to a cooled, stirred solution of 2'-deoxy-5-ethynyluridine (0.5 g, 1.98 mmols) in dry pyridine (5 ml) and stirring was maintained at room temperature for 3 hours. TLC in CH2Cl2 /MeOH (19:1) revealed complete reaction. The mixture was poured onto ice/water, methylene chloride added, the organic layer separated and washed with water, dried with sodium sulphate and evaporated to dryness. The residue was chromatographed on silica gel eluted with CH2Cl2 /MeOH. The first product was triturated with hexane to give 2'-deoxy-3',5'-di-O-pivaloyl-5-ethynyluridine. M.p. 151° C.

Workup

  1. customreaction
  2. additionadded
  3. customthe organic layer separated
  4. washwashed with water
  5. dry with materialdried with sodium sulphate
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel
  8. washeluted with CH2Cl2 /MeOH
  9. customThe first product was triturated with hexane

Sources & evidence

ORD record
ord-fc447fc2abeb4b1a988c53e72fbd08df
Source dataset
uspto-grants-1989_09
Patent number
US04863906

Reaction notes

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