Hydrochloric Acid → 1-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

HRID 528741Notes

Reaction equation

HRID 528741 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O.O1CCOCC1>[CH2:14]([O:21][C:22]([N:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 931923-azetidinecarboxylic Acid

Product 1

HCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To 500 mg (4.95 mmol) azetidine-3-carboxylic acid was added 10 mL dioxane and 10 mL H2O and the solution cooled to 0° C. 1.38 g (10 mmol) potassium carbonate was added followed by 0.78 mL (11 mmol) benzylchloroformate, and the reaction stirred at room temperature for 18 hours. The mixture was acidified with 25 mL 1 M HCl, extracted with DCM (2×20 mL), the combined organic layers dried over Na2SO4. After filtration the solvent was evaporated to give the desired product which was used in the next step without further purification.

Workup

  1. extractionextracted with DCM (2×20 mL)
  2. dry with materialthe combined organic layers dried over Na2SO4
  3. filtrationAfter filtration the solvent
  4. customwas evaporated

Sources & evidence

ORD record
ord-413a217f1ffa4340a526e9f499ea2226
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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