Chloroform → 3,5-Dioxohexanoic acid

HRID 1438832Notes

Reaction equation

HRID 1438832 reaction equation
C(CC1N([C@@H:9]2[O:15][C@H:14](CO)[C@@H:12](O)[C@H:10]2[OH:11])C=NC=1C(N)=O)#N.C([O:24][C:25](=[O:27])[CH3:26])(=O)C.C(Cl)(Cl)Cl>CN(C)C1C=CN=CC=1.CO>[CH3:9][C:10]([CH2:12][C:14]([CH2:26][C:25]([OH:24])=[O:27])=[O:15])=[O:11]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 7918Acetic Anhydride2×HCID 3008190HCID 3008190, compound

Product 1

HCID 54598443,5-Dioxohexanoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 887MethanolSolvent

Procedure

A suspension of 5-cyanomethyl-1-β-D-ribofuranosylimidazole-4-carboxamide (1.41 g, 5 mmol), acetic anhydride (15 ml) and p-dimethylaminopyridine (20 mg) was stirred at RT for 8 hr. Tlc (silica gel, CHCl3 --MeOH, 4:1) indicated three products. Additional p-dimethylaminopyridine (20 mg) and acetic anhydride (5 ml) was added and stirring continued at RT for 36 hr. The solution was evaporated in vacuo to a syrup which was dissolved in chloroform and placed on a column of silica gel (60 g). Elution with chloroform-methanol (20:1) provided the triacetate (2.0 g, 95%) as a white foam; pmr (DMSO-d6): δ 2.08, 2.10, 2.16 (s,3,COCH3), 4.40 (s,2,CH2), 6.13 (d,1,H1'), J = 5Hz, 7.39, 7.58 (s,2,NH), 8.19 (s,1,C2H).

Workup

  1. stirringstirring
  2. waitcontinued at RT for 36 hr
  3. customThe solution was evaporated in vacuo to a syrup which
  4. dissolutionwas dissolved in chloroform
  5. washElution with chloroform-methanol (20:1)

Sources & evidence

ORD record
ord-52d31cbc10834c2a93892e45e539da0b
Source dataset
uspto-grants-1977_11
Patent number
US04056674

Reaction notes

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