Sodium Hydroxide → HCID 69213875, compound

HRID 1392166Notes

Reaction equation

HRID 1392166 reaction equation
[OH-:1].[Na+].C[O:4][C:5]([C:7]1[CH:31]=[CH:30][C:10]([CH2:11][C:12]23[CH2:19][CH2:18][CH2:17][N:16]2[C:15](=[O:20])[N:14]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)[C:13]3=[O:29])=[CH:9][CH:8]=1)=[O:6]>CO.O.O>[Cl:28][C:23]1[CH:22]=[C:21]([NH:14][C:15]([N:16]2[CH2:17][CH2:18][CH2:19][C@@:12]2([CH2:11][C:10]2[CH:9]=[CH:8][C:7]([C:5]([OH:4])=[O:6])=[CH:31][CH:30]=2)[C:13]([OH:1])=[O:29])=[O:20])[CH:26]=[C:25]([Cl:27])[CH:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22479155HCID 22479155, compound

Product 1

HCID 69213875HCID 69213875, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
45 °C

Procedure

NaOH (0.406 g) was added to a solution of 5-(4-methoxycarbonylbenzyl)-3-(3,5-dichlorophenyl)-1,3-diazabicyclo[3.3.0]octane-2,4-dione (0.601 g) in MeOH/H2O (20 mL/4 mL) and the mixture was heated at 45° C. for 18 hours. The reaction mixture was cooled, acidified, diluted with water and extracted with EtOAc. The extract was washed with water, brine, dried (MgSO4), filtered, and concentrated. The residue was recrystallized from EtOAc/hexane (1:1) to give N-[N-(3,5-dichlorophenyl)carbamoyl]-2-(4-carboxybenzyl)proline (0.529 g). mp. 144.6° C.; MS (m/z) 459 (M++Na). (2) A mixture of the compound obtained above (0.074 g) and SOCl2 (1.0 mL) was heated at 100° C. for 1 hour. The solution was evaporated. The residue was dissolved in toluene, evaporated and dried under vacuum. The residue was dissolved in THF (4 mL) and the solution was added to an ice cold solution of dimethylamine (1 mL, 2M in THF) in THF (1 mL). The reaction mixture was stirred for 3 hour at room temperature and diluted with EtOAc and water. The organic layer was separated and washed with 0.5 N HCl (10 mL), water and brine. It was dried (MgSO4), filtered, and concentrated. Purification by chromatography (Silica gel: EtOAc, Chromatotron) afforded the titled compound (47 mg). MS (m/z) 468 (M++Na).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe extract was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-8332d6cb47e746d1a7f8c04a81582179
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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