3-(1-{3-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-2-hydroxy-ethylamino]-3-methyl-butyl}-5-methyl-1H-[1,2,4]triazol-3-yl)-benzoic acid trifluoroacetate → HCID 86607262, compound

HRID 29814Notes

Reaction equation

HRID 29814 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].C([O:15][C:16]1[CH:17]=[C:18]([CH:27]([OH:50])[CH2:28][NH:29][C:30]([CH3:49])([CH3:48])[CH2:31][CH2:32][N:33]2[C:37]([CH3:38])=[N:36][C:35]([C:39]3C=[C:41]([CH:45]=[CH:46][CH:47]=3)C(O)=O)=[N:34]2)[C:19]2[O:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=2[CH:26]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:50][CH:27]([C:18]1[C:19]2[O:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=2[CH:26]=[C:16]([OH:15])[CH:17]=1)[CH2:28][NH:29][C:30]([CH3:49])([CH3:48])[CH2:31][CH2:32][N:33]1[C:37]([CH3:38])=[N:36][C:35]([C:39]2[CH:47]=[CH:46][CH:45]=[CH:41][C:2]=2[C:3]([OH:5])=[O:4])=[N:34]1

Participants

5

Reactant 2

HCID 684986023-(1-{3-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-2-hydroxy-ethylamino]-3-methyl-butyl}-5-methyl-1H-[1,2,4]triazol-3-yl)-benzoic acid trifluoroacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 86607262HCID 86607262, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

250 mg (0.36 mmol) 3-(1-{3-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-2-hydroxy-ethylamino]-3-methyl-butyl}-5-methyl-1H-[1,2,4]triazol-3-yl)-benzoic acid trifluoroacetate are dissolved in 5 mL methanol and hydrogenated at ambient temperature and 2.5 bar hydrogen pressure in the presence of palladium on charcoal (10%). The catalyst is suction filtered, the filtrate is evaporated down and the residue is purified by chromatography (reverse phase, acetonitrile/water gradient with 0.1% trifluoroacetic acid). Yellow solid. Yield: 62 mg (28%, trifluoroacetate); mass spectroscopy [M+H]+=496.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated down
  3. customthe residue is purified by chromatography (reverse phase, acetonitrile/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-24cd195134234a718326444cfe00c09e
Source dataset
uspto-grants-2008_09
Patent number
US07423036B2

Reaction notes

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