Butyl nitrite → HCID 178476347, compound

HRID 2221083Notes

Reaction equation

HRID 2221083 reaction equation
[CH:1]1[N:9]=[C:8](N)[C:7]2[C:3](=[C:4]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[NH:5][N:6]=2)[N:2]=1.N([O:22][CH2:23][CH2:24]CC)=O>C1COCC1>[C:14]([O:19][C@@H:12]1[C@H:13]([O:18][C:12](=[O:19])[CH3:11])[C@@H:14]([CH2:16][O:17][C:23](=[O:22])[CH3:24])[O:15][C@H:11]1[C:4]1[C:3]2[N:2]=[CH:1][N:9]=[CH:8][C:7]=2[NH:6][N:5]=1)(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 10996Butyl nitriteHCID 447199Formycin

Product 1

HCID 178476347HCID 178476347, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2′,3′,5′-tri-O-acetyl-formycin A (prepared from formycin A by modification of the method from Synthesis (1989) 401) (1.1 g, 2.8 mmol) and n-butyl nitrite (2.6 ml, 22 mmol) in THF (30 ml) was heated at 50° C. for 25 h. After cooling to room temperature, the solvent was removed under reduced pressure. The mixture was dissolved in EtOH and reconcentrated (in each case twice). Silica gel chromatography using 2% MeOH in DCM gave compound (Ia) (0.49 g, 46%), the analysis of which confirmed the chemical identity with the product from method A.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe mixture was dissolved in EtOH
  4. customgave compound (Ia) (0.49 g, 46%)

Sources & evidence

ORD record
ord-db24caffb63c4db48e6a06edd0e15548
Source dataset
uspto-grants-2008_05
Patent number
US07368437B1

Reaction notes

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