Acetic Acid → 4-(4-{2-[2-hydroxy-2-(6-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxaazin-8-yl)-ethylamino]-2-methylpropyl}phenoxy)butyric acid

HRID 1827770Notes

Reaction equation

HRID 1827770 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:40])[CH2:21][NH:22][C:23]([CH3:39])([CH3:38])[CH2:24][C:25]2[CH:37]=[CH:36][C:28]([O:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:27][CH:26]=2)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[OH:40][CH:20]([C:11]1[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=[C:9]([OH:8])[CH:10]=1)[CH2:21][NH:22][C:23]([CH3:38])([CH3:39])[CH2:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22063479HCID 22063479, compound

Product 1

HCID 116267174-(4-{2-[2-hydroxy-2-(6-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxaazin-8-yl)-ethylamino]-2-methylpropyl}phenoxy)butyric acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.70 g (1.28 mmol) of 4-(4-{2-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-2-hydroxyethylamino]-2-methylpropyl}phenoxy)butyric acid is dissolved in 25 mL methanol and 2 mL acetic acid and hydrogenated in the presence of 150 mg palladium on charcoal (10%) at ambient temperature and normal pressure. The catalyst is filtered off and the filtrate is freed from solvent. The product is obtained by crystallization from a methanol-acetone mixture. Yield: 0.40 g (68%); melting point: 201° C.–204° C.; mass spectroscopy: [M+H]+=459.

Workup

  1. customat ambient temperature
  2. filtrationThe catalyst is filtered off
  3. customThe product is obtained by crystallization from a methanol-acetone mixture

Sources & evidence

ORD record
ord-3439bc5f6a6d474fa22b3a485b302b38
Source dataset
uspto-grants-2006_06
Patent number
US07056916B2

Reaction notes

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