Ethanol → 5-Hydroxy-8-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2H-1,4-benzoxazin-3(4H)-one acetate

HRID 749237Notes

Reaction equation

HRID 749237 reaction equation
C([O:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([CH:20]([OH:47])[CH2:21][N:22](CC2C=CC=CC=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([OH:50])C>C(OCC)(=O)C.[Pd]>[C:30]([OH:50])(=[O:29])[CH3:31].[OH:8][C:9]1[C:14]2[NH:15][C:16](=[O:19])[CH2:17][O:18][C:13]=2[C:12]([CH:20]([OH:47])[CH2:21][NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 693159345-(Benzyloxy)-8-(2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-hydroxyethyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 693198895-Hydroxy-8-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2H-1,4-benzoxazin-3(4H)-one acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(benzyloxy)-8-(2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-hydroxyethyl)-2H-1,4-benzoxazin-3(4H)-one (82 mg) in ethanol (10 ml) and ethyl acetate (2 ml) was stirrer under hydrogen in the presence of palladium on charcoal (50 mg) for 8 h. The reaction mixture was filtered and concentrated in vacuo. Mass directed auto-preparative chromatography afforded the title compound (13.7 mg). LCMS RT=2.62 min ES+ve 456 (MH)+

Workup

  1. customfor 8 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ea2cc142d164862a4d1bc00cfdbb9d5
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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