Citric Acid → HCID 57467236, compound

HRID 510520Notes

Reaction equation

HRID 510520 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1.C(N(C(C)C)CC)(C)C.[CH2:16]([S:19](Cl)(=[O:21])=[O:20])[CH2:17][CH3:18].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[CH2:16]([S:19]([N:2]1[CH2:5][CH:4]([OH:6])[CH2:3]1)(=[O:21])=[O:20])[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 57467236HCID 57467236, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution (0-5° C.) of azetidin-3-ol hydrochloride (1 g, 9.13 mmol) in 10 ml dichloromethane containing diisopropyl ethyl amine (2,391 ml, 13.69 mmol) was added dropwise a solution of propane-1-sulfonyl chloride (1,126 ml, 10.04 mmol) dissolved in 5 ml dichloromethane over an 1 h period. The mixture was allowed to warm up to room temperature and was stirred over night. Citric acid (10%) was added, extracted with dichloromethane, dried over MgSO4, filtered and the solvent was evaporated to obtain 597 mg of a yellow oil, which was purified by chromatography (yield 470 mg)

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-476b108e1b5f438aa7073d8fc4b62fc3
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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