Ethanol → HCID 67291669, compound

HRID 1689219Notes

Reaction equation

HRID 1689219 reaction equation
[N:1]([CH2:4][CH:5]([C:7]1[C:12]2[O:13][CH2:14][C:15](=[O:17])[NH:16][C:11]=2[C:10]([O:18][CH2:19][C:20]2C=CC=CC=2)=[CH:9][CH:8]=1)[OH:6])=[N+]=[N-].[H][H].C([OH:30])C>[Pd]>[C:19]([OH:30])(=[O:18])[CH3:20].[NH2:1][CH2:4][CH:5]([C:7]1[C:12]2[O:13][CH2:14][C:15](=[O:17])[NH:16][C:11]=2[C:10]([OH:18])=[CH:9][CH:8]=1)[OH:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 57988994HCID 57988994, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67291669HCID 67291669, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 8-(2-azido-1-hydroxyethyl)-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one, Isomer 1 (example 11, step g) (0.67 g) in ethanol (30 mL) with 10% palladium on carbon catalyst (0.210 g) was stirred vigorously under 4 bar pressure of hydrogen for 18 hours. The catalyst was filtered off and the solvent evaporated off under reduced pressure. The residue was dissolved in acetic acid (15 mL) and ethanol (15 mL) and the mixture stirred with 10% palladium on carbon catalyst (0.210 g) under 4 bar pressure of hydrogen for 18 hours. The mixture was filtered and fresh 10% palladium on carbon catalyst (0.210 g) was added and stirring under 4 bar pressure of hydrogen was continued for 18 hours. The mixture was filtered and fresh 10% palladium on carbon catalyst (0.210 g) added and stirring under 4 bar pressure of hydrogen was continued for 18 hours. The mixture was filtered and the solvent removed under reduced pressure. The residue was triturated with acetonitrile (30 mL) to afford the subtitled compound. Yield 0.33 g.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated off under reduced pressure
  3. dissolutionThe residue was dissolved in acetic acid (15 mL)
  4. filtrationThe mixture was filtered
  5. additionfresh 10% palladium on carbon catalyst (0.210 g) was added
  6. stirringstirring under 4 bar pressure of hydrogen
  7. waitwas continued for 18 hours
  8. filtrationThe mixture was filtered
  9. additionfresh 10% palladium on carbon catalyst (0.210 g) added
  10. stirringstirring under 4 bar pressure of hydrogen
  11. waitwas continued for 18 hours
  12. filtrationThe mixture was filtered
  13. customthe solvent removed under reduced pressure
  14. customThe residue was triturated with acetonitrile (30 mL)

Sources & evidence

ORD record
ord-fe8f805e2db3453c93b89118262f5669
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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