Acetic Acid → (R)-1-(4-bromo-benzoyl)-2-methyl-azetidine-2-carboxylic acid

HRID 408582Notes

Reaction equation

HRID 408582 reaction equation
C[O:2][C:3]([C@@:5]1([CH3:9])[CH2:8][CH2:7][NH:6]1)=[O:4].[OH-].[Na+].[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.C(O)(=O)C>O>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([N:6]2[CH2:7][CH2:8][C@:5]2([CH3:9])[C:3]([OH:2])=[O:4])=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 685154-Bromobenzoyl chlorideHCID 70556683methyl (2R)-2-methylazetidine-2-carboxylate

Product 1

HCID 70557656(R)-1-(4-bromo-benzoyl)-2-methyl-azetidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (R)-2-methyl-azetidine-2-carboxylic acid methyl ester (1 eq.) in water were added aqueous NaOH (1M) (3 eq.) then 4-bromo-benzoyl-chloride (1 eq.) dropwise. The reaction was stirred for 4 h at 20° C. The reaction was neutralised with acetic acid. The solvent was partially removed under reduced pressure and the crude was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with DCM/MeOH/AcOEt/AcOH/iPr2O: 95/5/98/2/300) to afford (R)-1-(4-bromo-benzoyl)-2-methyl-azetidine-2-carboxylic acid.

Workup

  1. customThe solvent was partially removed under reduced pressure
  2. extractionthe crude was extracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by chromatography on silica gel (elution with DCM/MeOH/AcOEt/AcOH/iPr2O: 95/5/98/2/300)

Sources & evidence

ORD record
ord-94275a0954b04b7baad270064a8b1dde
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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