Acetic Acid → HCID 67292487, compound

HRID 470994Notes

Reaction equation

HRID 470994 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]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[OH:6])=[N+]=[N-].[H][H].[C:28]([OH:31])(=[O:30])[CH3:29]>C(O)C.[Pd]>[C:28]([OH:31])(=[O:30])[CH3:29].[NH2:1][CH2:4][C@H: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

6

Reactant 3

HCID 176Acetic AcidHCID 57988994HCID 57988994, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67292487HCID 67292487, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8-(2-azido-1-hydroxyethyl)-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one, Isomer 2 (example 13, step a) (0.72 g) in a mixture of acetic acid (10 mL) and ethanol (10 mL) was stirred vigorously with 10% palladium on carbon catalyst (0.225 g) under 4 bar pressure of hydrogen for 18 hours. The mixture was filtered and fresh 10% palladium on carbon catalyst (0.225 g) 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 (0.225 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 0.28 g.

Workup

  1. filtrationThe mixture was filtered
  2. additionfresh 10% palladium on carbon catalyst (0.225 g) added
  3. filtrationThe mixture was filtered
  4. additionfresh 10% palladium on carbon catalyst (0.225 g) added
  5. stirringstirring under 4 bar pressure of hydrogen
  6. waitwas continued for 18 hours
  7. filtrationThe mixture was filtered
  8. customthe solvent removed under reduced pressure
  9. customThe residue was triturated with acetonitrile (30 mL)

Sources & evidence

ORD record
ord-5b984b0365fb4222ad88a72894e81e6d
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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