Hydrochloric Acid → 1-Boc-Azetidine-3-carboxylic acid

HRID 384846Notes

Reaction equation

HRID 384846 reaction equation
[C:1]([O:5][C:6]([O:8]C([O-])=O)=O)([CH3:4])([CH3:3])[CH3:2].[NH:12]1[CH2:15][CH:14]([C:16]([OH:18])=[O:17])[CH2:13]1.C(=O)([O-])[O-].[K+].[K+].Cl>O.C1COCC1>[C:1]([O:5][C:6]([N:12]1[CH2:15][CH:14]([C:16]([OH:18])=[O:17])[CH2:13]1)=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 931923-azetidinecarboxylic AcidHCID 22064466Tert-butyldicarbonate

Product 1

HCID 27559811-Boc-Azetidine-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of t-butyldicarbonate (21.15 g) and THF (170 ml) was added under ice cooling to a mixture of azetidine-3-carboxylic acid (9.80 g), potassium carbonate (26.8 g) and water (150 ml). After stirring the reaction mixture at room temperature for 20 hours, the mixture was adjusted to pH 4 using 2 mol/L hydrochloric acid, extracted with chloroform, the organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was crystallized with a mixed solution of hexane and ethyl acetate to obtain 19.5 g of 1-(t-butoxycarbonyl)azetidine-3-carboxylic acid.

Workup

  1. extractionextracted with chloroform
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was crystallized with a mixed solution of hexane and ethyl acetate

Sources & evidence

ORD record
ord-d209c5fdb7184c08af6277388a9ed033
Source dataset
uspto-grants-2013_02
Patent number
US08367835B2

Reaction notes

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