Hydrochloric Acid → HCID 22479160, compound

HRID 1392162Notes

Reaction equation

HRID 1392162 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:36]=[CH:35][C:14]([CH2:15][C:16]23[C:24](=[O:25])[N:23]([C:26]4[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=4)[C:22](=[O:34])[N:21]2[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:13][CH:12]=1)=[O:4].[OH-].[Na+].Cl>CO.O>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C:16]23[C:24](=[O:25])[N:23]([C:26]4[CH:27]=[C:28]([Cl:33])[CH:29]=[C:30]([Cl:32])[CH:31]=4)[C:22](=[O:34])[N:21]2[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:35][CH:36]=1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22479129HCID 22479129, compound

Product 1

HCID 22479160HCID 22479160, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A solution of 6-[4-(2-methoxycarbonylphenyl)benzyl]-8-(3,5-dichlorophenyl)-1,8-diazabicyclo[4.3.0]nonane-7,9-dione (0.141 g) in MeOH/H2O (5/1 mL) containing NaOH (0.087 g) was heated at 50° C. for 2 h. The reaction mixture was cooled in ice and acidified with 0.5 N HCl. It was extracted with EtOAc and the extract was washed with water, brine, dried (MgSO4), filtered, and concentrated. Purification by chromatography (Silica gel: CHCl3/MeOH: 100/1 to 50/1, Chromatotron) afforded the titled compound (114 mg). MS (m/z) 531 (M++Na).

Workup

  1. temperatureThe reaction mixture was cooled in ice
  2. extractionIt was extracted with EtOAc
  3. washthe extract was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (Silica gel: CHCl3/MeOH: 100/1 to 50/1, Chromatotron)

Sources & evidence

ORD record
ord-90d17757556344fc9a2511ea7beaf986
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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