Potassium Hydroxide → Ribavirin

HRID 1904892Notes

Reaction equation

HRID 1904892 reaction equation
[C@@H:1]1([N:10]2C3N=C(N)[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[NH:21]1C=NC(C(N)=O)=N1.[OH-].[K+]>>[CH:11]1[N:10]([C@@H:1]2[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]2[OH:3])[N:21]=[C:13]([C:14]([NH2:16])=[O:15])[N:12]=1

Participants

4

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 135398635Guanosine2×HCID 178513825HCID 178513825, compound2×

Product 1

HCID 37542Ribavirin

Procedure

Bioconversion media were prepared as in Example 1, except the initial amounts of guanosine and 1,2,4-triazole-3-carboxamide were 40 millimoles. The initial pH of each flask was adjusted to pH 7.2 with potassium hydroxide. The bioconversions were initiated as in Example 1, except that the temperature was 70° C. The cells were added promptly as the temperature reached 70° C. to avoid gelling of the bioconversion mixture. Forty millimole additions of both guanosine and 1,2,4-triazole-3-carboxamide were made at 6 and 12 hours into the bioconversion. Thus after the second addition, a total of 120 millimoles of the two reactants had been added. Potassium hydroxide was added at 6 hours to adjust the pH from 6.7 to 7.2.

Workup

  1. customBioconversion media were prepared as in Example 1
  2. customwas 70° C
  3. additionThe cells were added promptly as the temperature
  4. customreached 70° C.
  5. customwere made at 6 and 12 hours into the bioconversion
  6. additionThus after the second addition

Sources & evidence

ORD record
ord-a8db47e2bce94be39c275f0501d0803f
Source dataset
uspto-grants-1989_06
Patent number
US04840898

Reaction notes

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