Sodium Hydroxide → HCID 18518335, compound

HRID 1369262Notes

Reaction equation

HRID 1369262 reaction equation
C([C:3]1[C:13]2[CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[O:8][C:7]=2[CH:6]=[C:5]([O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][CH3:32])[N:26]=2)[CH:4]=1)C.[OH-].[Na+]>CCO>[CH3:32][NH:31][C:27]1[N:26]=[C:25]([CH2:24][CH2:23][O:22][C:5]2[CH:4]=[CH:3][C:13]3[CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[C:10]4[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=4[O:8][C:7]=3[CH:6]=2)[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585481HCID 86585481, compound

Product 1

HCID 18518335HCID 18518335, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (±)-10,11-dihydro-3-[2-[6(methylamino)pyridin-2-yl]-1-ethoxy]dibenzo[b,f]oxepine-10-acetic acid (0.26 mmole) and 0.991 N NaOH (0.525 mL, 0.52 mmole) in absolute EtOH (2 mL) was warmed in an oil bath set at 50° C. After 20 hr, the reaction was concentrated on the rotavap and the residue was dissolved in H2O (1.5 mL). The solution was filtered to remove insoluble material, and the filtrate was carefully neutralized by dropwise addition of 1.0 N HCl. The precipitate was collected and dried in high vacuum to afford the title compound (72 mg, 30% for 2 steps) as an off-white solid: MS (ES) m/e 405.0 (M+H)+. Anal. Calcd for C24H24N2O4.1.25HCl. 0.25H2O: C, 63.42; H, 5.71; N, 6.16. Found: C, 63.35; H, 5.9; N, 6.16.

Workup

  1. temperaturewas warmed in an oil bath
  2. customset at 50° C
  3. concentrationthe reaction was concentrated on the rotavap
  4. dissolutionthe residue was dissolved in H2O (1.5 mL)
  5. filtrationThe solution was filtered
  6. customto remove insoluble material
  7. additionthe filtrate was carefully neutralized by dropwise addition of 1.0 N HCl
  8. customThe precipitate was collected
  9. customdried in high vacuum

Sources & evidence

ORD record
ord-0a5f3a382fb349839efa15dd06629ef8
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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