Tetrahydrofuran → HCID 69944833, compound

HRID 1596183Notes

Reaction equation

HRID 1596183 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][CH:6]1[CH2:9][NH:8][CH2:7]1)[CH3:2].C1COCC1.[C:16](Cl)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(=O)(O)[O-].[Na+]>[CH2:19]([O:18][C:16]([N:8]1[CH2:9][CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:10])[CH2:7]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 54328202HCID 54328202, compound

Product 1

HCID 69944833HCID 69944833, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirring mixture of azetidin-3-yl-acetic acid ethyl ester (1.0 g, 6.98 mmol), in saturated aqueous sodium bicarbonate (5 mL) and THF (5 mL) at 0° C. was added carbobenzyloxy chloride (1.1 mL, 7.68 mmol) dropwise. The ice bath was removed and the reaction mixture was stirred at room temperature for 2 hrs, then extracted with ethyl acetate acetate (3×20 mL). The combined ethyl acetate layer was washed with water (10 mL), brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel, eluting with 20% ethyl acetate in hexane to give 0.30 g of the title compound.

Workup

  1. customThe ice bath was removed
  2. extractionextracted with ethyl acetate acetate (3×20 mL)
  3. washThe combined ethyl acetate layer was washed with water (10 mL), brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9027704db92841c9a01a01c25ca5ef3d
Source dataset
uspto-grants-2001_09
Patent number
US06291457B1

Reaction notes

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