Hydroxylamine → HCID 88793643, compound

HRID 1391080Notes

Reaction equation

HRID 1391080 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].[NH2:23][OH:24]>C(O)C>[NH2:19][C:18]1[C:3]2[C:2]([C:21](=[N:23][OH:24])[NH2:22])=[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 787HydroxylamineHCID 3011114-Amino-2-chloro-7-pentofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Product 1

HCID 88793643HCID 88793643, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chlorotoyocamycin (6, 250 mg) and solid hydroxylamine (250 mg) were added to 20 ml of absolute ethanol and the mixture was heated at reflux temperature for 30 min. The solution was allowed to stand at -10° for 24 hr and the solid was collected by filtration, washed with 10 ml of ice cold ethanol and recrystallized from water to yield 200 mg (76%) of 10, mp 170° dec.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 30 min
  3. filtrationthe solid was collected by filtration
  4. washwashed with 10 ml of ice cold ethanol
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-bd533fd830984f44a58a7e264760dd67
Source dataset
uspto-grants-1979_02
Patent number
US04140851

Reaction notes

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