Hydrochloric Acid → HCID 71246839, compound

HRID 1487015Notes

Reaction equation

HRID 1487015 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([F:20])([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-:21].[Na+].Cl.C([OH:26])C>>[CH:1]([N:14]1[CH2:17][C:16]([F:20])([C:18]([OH:26])=[O:21])[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 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 58661631HCID 58661631, compound

Product 1

HCID 71246839HCID 71246839, compoundYield 13%

Procedure

1-Benzhydryl-3-fluoroazetidine-3-carbonitrile (3.5 g, 1.0 eq.) was dissolved in ethanol, and aq. NaOH solution (1N) was added. The reaction mixture was refluxed for 5 h, then was allowed to cool to room temperature, at which temperature, it was acidified with dilute HCl (pH=3) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure to obtain 0.5 g of 1-benzhydryl-3-fluoroazetidine-3-carboxylic acid (13% yield). The product was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d944d8b5967743eb8861df80baeb241d
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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