HCID 178508933, compound → 1,1'-Carbonyldiimidazole

HRID 2224036Notes

Reaction equation

HRID 2224036 reaction equation
[CH:1]1[N:5]([CH2:6][O:7]CCO)[C:4]2N=C(N)N=C(O)[C:3]=2[N:2]=1>O1CCCC1>[C:6]([N:5]1[CH:4]=[CH:3][N:2]=[CH:1]1)([N:2]1[CH:3]=[CH:4][N:5]=[CH:1]1)=[O:7]

Participants

3

Reactant 1

HCID 178508933HCID 178508933, compound

Product 1

HCID 682631,1'-CarbonyldiimidazoleYield 200%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-acetyl-S-(4-nitroxybutyroyl)cisteine (2.8 g, 9.6 mmoles) and 1,1′-carbonyldiimidazole (1.55 g, 9.6 mmoles) in tetrahydrofuran (50 ml) is prepared and left under stirring at room temperature for 1 hour. The reaction mixture is treated with acyclovir (2.16 g, 9.6 mmoles). After 6 hours of reaction at room temperature, the solution is evaporated at reduced pressure, the obtained residue treated with ethyl acetate and washed with brine. The organic phase is anhydrified with sodium sulphate and then dried under vacuum. The obtained residue is purified by chromatography on silica gel column eluting with ethyl acetate. 9-[[2-[N-acetyl-S-(4-nitroxybutyroyl)cisteinyl-]ethoxy]methyl]guanine is obtained. Yields: 9%.

Workup

  1. waitleft
  2. customAfter 6 hours of reaction at room temperature
  3. customthe solution is evaporated at reduced pressure
  4. additionthe obtained residue treated with ethyl acetate
  5. washwashed with brine
  6. customdried under vacuum
  7. customThe obtained residue is purified by chromatography on silica gel column
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f6370b2707cf492b9ee7119f2e6e575d
Source dataset
uspto-grants-2008_05
Patent number
US07378412B2

Reaction notes

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