Hydrochloric Acid → 1-[(4-Iodophenyl)sulfonyl]azetidine-3-carboxylic acid

HRID 1913167Notes

Reaction equation

HRID 1913167 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.[OH-].[Na+].[I:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.Cl>C(Cl)Cl.C(Cl)Cl.O.O>[I:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:2]2[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73994-Iodobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 13374356Azetidine-3-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 584945631-[(4-Iodophenyl)sulfonyl]azetidine-3-carboxylic acidYield 44%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

To a stirred solution of azetidine-3-carboxylic acid hydrochloride (1.0 g, 7.27 mmol) in DCM (25 mL) is added 5N aqueous NaOH (10 mL) and water (10 mL). p-Iodobenzenesulfonyl chloride (2.41 g, 7.98 mmol) is added portionwise. After 18 h the reaction mixture is diluted with DCM/water. The basic aqueous layer is acidified with 5N aqueous HCl. The resultant precipitate is filtered, washed with water and MeCN. Drying in air gives 1.17 g (44%) of 1-[(4-iodophenyl)sulfonyl]azetidine-3-carboxylic acid. m/z=368 [M++H].

Workup

  1. filtrationThe resultant precipitate is filtered
  2. washwashed with water and MeCN
  3. customDrying in air

Sources & evidence

ORD record
ord-d56519c21a7d4a808c277a818728107e
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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