Sodium Hydroxide → HCID 10530330, compound

HRID 441246Notes

Reaction equation

HRID 441246 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:41])[C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:40])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)=[CH:21][CH:20]=2)[CH2:10][CH2:9][C:8]1=[O:42])=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:41])[C:19]2[CH:20]=[CH:21][C:22]([NH:25][C:26](=[O:40])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)=[CH:23][CH:24]=2)[CH2:10][CH2:9][C:8]1=[O:42])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10816720HCID 10816720, compound

Product 1

HCID 10530330HCID 10530330, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 1-ethoxycarbonylmethyl-5-{4-[2-(4methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (240 mg), 1N sodium hydroxide aqueous solution (2 ml) and ethanol (5 ml) was stirred for 1 hour at ambient temperature. The reaction was quenched with 1N hydrochloric acid (2 ml) and ethanol was removed. The residue was diluted with ethyl acetate and the solution was washed with brine, and the solution was dried over magnesium sulfate. Filtering and the removal of solvents afforded a crude product. The crude product was triturated with a mixture of diisopropyl ether and diethyl ether (1:1) to give 1-carboxymethyl-5-{4-[2-(4methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (217 mg) as a white powder.

Workup

  1. customThe reaction was quenched with 1N hydrochloric acid (2 ml) and ethanol
  2. customwas removed
  3. additionThe residue was diluted with ethyl acetate
  4. washthe solution was washed with brine
  5. dry with materialthe solution was dried over magnesium sulfate
  6. filtrationFiltering
  7. customthe removal of solvents
  8. customafforded a crude product
  9. customThe crude product was triturated with a mixture of diisopropyl ether and diethyl ether (1:1)

Sources & evidence

ORD record
ord-92698a467f1848beb389bea87c981aeb
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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