HCID 21072812, compound → HCID 21072816, compound

HRID 1867337Notes

Reaction equation

HRID 1867337 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:45])[CH2:21][NH:22][C:23]([CH3:44])([CH3:43])[CH2:24][CH2:25][N:26]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[C:29]([CH2:39][CH2:40][CH3:41])([CH2:36][CH2:37][CH3:38])[O:28][C:27]2=[O:42])[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:45][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]([CH3:43])([CH3:44])[CH2:24][CH2:25][N:26]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]([CH2:39][CH2:40][CH3:41])([CH2:36][CH2:37][CH3:38])[O:28][C:27]1=[O:42]

Participants

5

Reactant 2

HCID 21072812HCID 21072812, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21072816HCID 21072816, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 270 mg (0.438 mmol) 1-{3-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-2-hydroxyethylamino]-3-methylbutyl}-4,4-dipropyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one and 27 mg Pd/C (10%) in MeOH (8 mL) is hydrogenated at RT and 1 bar hydrogen pressure for 3 hours. The catalyst is filtered off through CELITE® filter aid and washed with MeOH (5 mL) and the filtrate is concentrated by evaporation in vacuo. The residue is dissolved in EtOAc/dichloromethane (1:1, 10 mL), acidified to pH 2 by the addition of HCl solution (saturated in EtOAc) and concentrated by evaporation in vacuo. The residue is triturated with ether, filtered and dried in vacuo. Yield: 80 mg (33%; hydrochloride), HPLC-MS: Rt=12.8 min. (method A), ESI-MS: [M+H]+=526.

Workup

  1. customis hydrogenated at RT
  2. filtrationThe catalyst is filtered off through CELITE®
  3. filtrationfilter aid
  4. washwashed with MeOH (5 mL)
  5. concentrationthe filtrate is concentrated by evaporation in vacuo
  6. dissolutionThe residue is dissolved in EtOAc/dichloromethane (1:1, 10 mL)
  7. additionacidified to pH 2 by the addition of HCl solution (saturated in EtOAc)
  8. concentrationconcentrated by evaporation in vacuo
  9. customThe residue is triturated with ether
  10. filtrationfiltered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-abbd124e5161487c819e01c0a36a0571
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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