Lithium Hydroxide → HCID 22479139, compound

HRID 1392175Notes

Reaction equation

HRID 1392175 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]23[CH2:14][C:13](=[CH:15][C:16]([O:18]C)=[O:17])[CH2:12][N:11]2[C:10](=[O:20])[N:9]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)[C:8]3=[O:29])=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]23[CH:14]=[C:13]([CH2:15][C:16]([OH:18])=[O:17])[CH2:12][N:11]2[C:10](=[O:20])[N:9]([C:21]2[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=2)[C:8]3=[O:29])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69215852HCID 69215852, compound

Product 1

HCID 22479139HCID 22479139, compoundYield 11.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-Bromobenzyl)-3-(3,5-dichlorophenyl)-7-methoxycarbonylmethylene-1,3-diazabicyclo[3.3.0]octane-2,4-dione (0.564 g) in THF (4 mL) and methanol (1 mL) at 0° C. was added 2N LiOH (1.20 mL). After 2 hours, the reaction mixture was concentrated and the residue was suspended in 1 N HCl and filtered. A solution of the filtrate (0.10 g) in thionyl chloride (5 mL) was refluxed for 30 minutes. The reaction mixture was concentrated and the residue was diluted with EtOAc and water. The organic solution was collected and dried (Na2SO4), filtered, and concentrated. Purification by chromatography (Silica gel: 4% MeOH/CH2Cl2, Chromatotron) afforded 0.063 g of the titled compound. MS (m/z) 509 (MH+), mp 101.5° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. filtrationfiltered
  3. temperatureA solution of the filtrate (0.10 g) in thionyl chloride (5 mL) was refluxed for 30 minutes
  4. concentrationThe reaction mixture was concentrated
  5. additionthe residue was diluted with EtOAc and water
  6. customThe organic solution was collected
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by chromatography (Silica gel: 4% MeOH/CH2Cl2, Chromatotron)

Sources & evidence

ORD record
ord-a85108a5e75246d4bd175bad70fe9bca
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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