Hydrogen Peroxide → HCID 22806998, compound

HRID 1391079Notes

Reaction equation

HRID 1391079 reaction equation
[CH:1]1[N:5]([CH:6]2[O:10][CH:9]([CH2:11][OH:12])[CH:8]([OH:13])[CH:7]2[OH:14])[C:4]2[N:15]=[C:16]([Cl:20])[N:17]=[C:18]([NH2:19])[C:3]=2[C:2]=1[C:21]#[N:22].[OH:23]O>[OH-].[NH4+]>[NH2:19][C:18]1[C:3]2[C:2]([C:21]([NH2:22])=[O:23])=[CH:1][N:5]([C@@H:6]3[O:10][C@H:9]([CH2:11][OH:12])[C@@H:8]([OH:13])[C@H:7]3[OH:14])[C:4]=2[N:15]=[C:16]([Cl:20])[N:17]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide4×HCID 3011114-Amino-2-chloro-7-pentofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Product 1

HCID 22806998HCID 22806998, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

2-Chlorotoyocamycin (6, 200 mg) was suspended in 40 ml of conc. ammonium hydroxide and 4 ml of 30% hydrogen peroxide were added. The mixture was stirred at room temperature for 2 hr and 2 more ml of 30% hydrogen peroxide were added. Stirring at room temperature was continued for 2 more hours and 2 more ml of 30% hydrogen peroxide were added and the solution was stirred at room temperature for an additional 12 hr. One more ml of hydrogen peroxide was added and stirring at room temperature was continued for an additional hour and the solution was evaporated to dryness in vacuo. The residue was coevaporated first with 40 ml of ethanol and then 40 ml of acetone. The residue was suspended in 50 ml of chloroform, the solid was collected by filtration, washed with 25 ml of chloroform and air dried. The product was then crystallized from 10 ml of absolute ethanol to yield, after drying the sample in an Abderhalden apparatus for 2 hr in vacuo at 110°, 100 mg (47%) of 8, mp 175° dec.

Workup

  1. stirringStirring at room temperature
  2. additionwere added
  3. stirringthe solution was stirred at room temperature for an additional 12 hr
  4. stirringstirring at room temperature
  5. waitwas continued for an additional hour
  6. customthe solution was evaporated to dryness in vacuo
  7. filtrationthe solid was collected by filtration
  8. washwashed with 25 ml of chloroform and air
  9. customdried
  10. customThe product was then crystallized from 10 ml of absolute ethanol
  11. customto yield
  12. customafter drying the sample in an Abderhalden apparatus for 2 hr in vacuo at 110°

Sources & evidence

ORD record
ord-b9b1a00e52454c9abca05c0f03b24ec9
Source dataset
uspto-grants-1979_02
Patent number
US04140851

Reaction notes

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