Hydrochloric Acid → HCID 83818271, compound

HRID 2363267Notes

Reaction equation

HRID 2363267 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([C:12](=[O:16])COC)=[CH:8][CH:7]=2)[CH2:3]1.[OH2:17].[OH-].[Li+].Cl>O.CO.C1COCC1>[OH:1][CH:2]1[CH2:3][N:4]([C:6]2[CH:7]=[CH:8][C:9]([C:12]([OH:16])=[O:17])=[CH:10][CH:11]=2)[CH2:5]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 71208001HCID 71208001, compound

Product 1

HCID 83818271HCID 83818271, compoundYield 94.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-[4-(3-hydroxyazetidin-1-yl)phenyl]-2-methoxyethanone (1.33 g, 6.00 mmol) and lithium hydroxide monohydrate (504 mg, 12.0 mmol) in water (4 mL), methanol (3 mL) and THF (6 mL) was stirred at 40° C. overnight. The mixture was neutralized with 3 N HCl aqueous solution (˜4 mL) to pH about 7, extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product (1.10 g, 94.9%) which was directly used in next step reaction without further purification. LCMS (M+H)+: m/z=194.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f993a0848cb48ff982f1dacc0d45410
Source dataset
uspto-grants-2014_04
Patent number
US08691807B2

Reaction notes

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