Sodium Hydroxide → HCID 22105438, compound

HRID 1456641Notes

Reaction equation

HRID 1456641 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:9][CH:8]([NH:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:7]1=[O:34])C.[OH-].[Na+]>O1CCOCC1>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]2[N:6]([CH2:5][C:4]([OH:35])=[O:3])[C:7](=[O:34])[CH:8]([NH:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:9]=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:11]=2[CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67695547HCID 67695547, compound

Product 1

HCID 22105438HCID 22105438, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of rac-7-chloro-5-(2-chlorophenyl)-3-[[(1,1-dimethylethoxy)-carbonyl]methylamino]-2,3-dihydro-2-oxo-1H-1-benzazepine-1-acetic acid ethyl ester (1.50 g, 2.89 mmole) in 11 mL of dioxane was added 1.0N aqueous sodium hydroxide solution (4.2 mL, 4.2 mmole). After stirring for 3 hours at ambient temperature, the solution was concentrated under high vacuum. The residue was dissolved in 40 mL of water and acidified to pH 3 with 1N HCl. A thick precipitate formed which was extracted into 100 mL of ethyl acetate. The organic phase was removed, washed with brine, dried (sodium sulfate) and concentrated. The crude product was crystallized from ether-petroleum ether yielding 1.24 g (87%) of white solid. IR (KBr) 1739, 1697 cm-1. Mass spec (FAB+, m/z 491). (Found: C, 58.90; H, 5.10; N, 5.40; Cl, 14.13. Calc for C4H24N2O5Cl2 : C, 58.67; H, 4.92; N, 5.70; Cl, 14.43).

Workup

  1. concentrationthe solution was concentrated under high vacuum
  2. dissolutionThe residue was dissolved in 40 mL of water
  3. customA thick precipitate formed which
  4. extractionwas extracted into 100 mL of ethyl acetate
  5. customThe organic phase was removed
  6. washwashed with brine
  7. dry with materialdried (sodium sulfate)
  8. concentrationconcentrated
  9. customThe crude product was crystallized from ether-petroleum ether yielding 1.24 g (87%) of white solid

Sources & evidence

ORD record
ord-926cfda8f5d74eeaa70e5b9fba23b7d9
Source dataset
uspto-grants-1998_12
Patent number
US05843941

Reaction notes

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