HCID 21072810, compound → HCID 21072841, compound

HRID 1867319Notes

Reaction equation

HRID 1867319 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:22]([OH:45])[CH2:23][NH:24][C:25]([CH3:44])([CH3:43])[CH2:26][CH2:27][N:28]2[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[C:31]([CH2:40][CH3:41])([CH2:38][CH3:39])[O:30][C:29]2=[O:42])[C:12]2[O:17][C:16]([CH3:19])([CH3:18])[C:15](=[O:20])[NH:14][C:13]=2[CH:21]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:40]([C:31]1([CH2:38][CH3:39])[O:30][C:29](=[O:42])[N:28]([CH2:27][CH2:26][C:25]([NH:24][CH2:23][CH:22]([OH:45])[C:11]2[C:12]3[O:17][C:16]([CH3:18])([CH3:19])[C:15](=[O:20])[NH:14][C:13]=3[CH:21]=[C:9]([OH:8])[CH:10]=2)([CH3:43])[CH3:44])[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]1=2)[CH3:41]

Participants

4

Reactant 1

HCID 21072810HCID 21072810, compound

Product 1

HCID 21072841HCID 21072841, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

130 mg (0.21 mmol) 1-{3-[2-(6-benzyloxy-2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-diethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one are dissolved in 5 mL methanol and hydrogenated in the presence of palladium on charcoal (10%) at ambient temperature. The catalyst is suction filtered, the filtrate is evaporated down and the residue is purified by chromatography (Reverse phase; acetonitrile/water gradient). White solid. Yield: 41 mg (37%); mass spectroscopy [M+H]+=526.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated down
  3. customthe residue is purified by chromatography (Reverse phase; acetonitrile/water gradient)

Sources & evidence

ORD record
ord-25e59f432214471b8c8342bacf18630c
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

Loading…