Lithium hydroxide, monohydrate → 1-Cbz-3-azetidineacetic acid

HRID 1596184Notes

Reaction equation

HRID 1596184 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([CH2:15][C:16]([O:18]CC)=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([CH2:15][C:16]([OH:18])=[O:17])[CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69944833HCID 69944833, compound

Product 1

HCID 404294021-Cbz-3-azetidineacetic acidYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-ethoxycarbonylmethylazetidine-1-carboxylic acid benzyl ester (0.30 g, 1.1 mmol), and lithium hydroxide monohydrate (0.091 g, 2.2 mmol) in TBF (3 mL) and water (1 mL) was stirred under argon at room temperature for 1 hr. After acidification with 2 M aqueous hydrochloric acid (10 mL), the reaction mixture was extracted with ethyl acetate (3×20 ml). The combined ethyl acetate layers were washed with water (10 mL), brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give 0.27 g of the title compound.

Workup

  1. extractionAfter acidification with 2 M aqueous hydrochloric acid (10 mL), the reaction mixture was extracted with ethyl acetate (3×20 ml)
  2. washThe combined ethyl acetate layers were washed with water (10 mL), brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-73ff499ea5da4b9bb8089b6cee798909
Source dataset
uspto-grants-2001_09
Patent number
US06291457B1

Reaction notes

Loading…