Water → HCID 70663158, compound

HRID 1258011Notes

Reaction equation

HRID 1258011 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[CH:22][C:21]=2[Br:33])([C:18]#N)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:34].[Na+].[OH2:36]>CCO>[CH:1]([N:14]1[CH2:17][C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[CH:22][C:21]=2[Br:33])([C:18]([OH:36])=[O:34])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58079830HCID 58079830, compound

Product 1

HCID 70663158HCID 70663158, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-benzhydryl-3-(2-bromo-4-(diethoxymethyl)phenyl)-azetidine-3-carbonitrile (Preparation 16, 13.5 g, 26.7 mmol) in EtOH (150 mL) was added aq NaOH (85 mL of a 25% wt. solution). The reaction mixture was heated to reflux for 36 hours. Contents were concentrated under vacuum to remove EtOH to a concentration of ˜100 mL and solution became cloudy. The residue was placed in an ice bath and cooled. The pH of the residue was lowered to ˜5-7 by the slow addition of 3M HCl at which time a precipitate formed. Additional water was added and the mixture was stirred for 15 minutes and filtered. The precipitate was re-dissolved in EtOAc (250 mL) and washed with saturated NH4Cl and brine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 36 hours
  3. concentrationContents were concentrated under vacuum
  4. customto remove EtOH to a concentration of ˜100 mL and solution
  5. customThe residue was placed in an ice bath
  6. temperaturecooled
  7. additionThe pH of the residue was lowered to ˜5-7 by the slow addition of 3M HCl at which time a precipitate
  8. customformed
  9. filtrationfiltered
  10. dissolutionThe precipitate was re-dissolved in EtOAc (250 mL)
  11. washwashed with saturated NH4Cl and brine

Sources & evidence

ORD record
ord-08c4f7bee5d046e8823704b2a1202e1a
Source dataset
uspto-grants-2013_06
Patent number
US08466115B2

Reaction notes

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