Hydrochloric Acid → (2S)-1-(alpha-Toluenesulfonyl)azetidine-2-carboxylic acid

HRID 1264474Notes

Reaction equation

HRID 1264474 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[S:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:11])=[O:10])=[O:4].[Li+].[OH-].Cl>CO.O>[C:13]1([CH2:12][S:9]([N:6]2[CH2:7][CH2:8][C@H:5]2[C:3]([OH:4])=[O:2])(=[O:11])=[O:10])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59049296HCID 59049296, compound

Product 1

HCID 59049318(2S)-1-(alpha-Toluenesulfonyl)azetidine-2-carboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of (2S)-Methyl-1-(α-toluenesulfonyl)azetidine-2-carboxylate from Reference Example 7 (378.4 mg; 1.40 mmol) in methanol (7.0 mL) was added 1N LiOH in water (2.6 mL) at about 0° C. The mixture was warmed to about room temperature and stirred under argon overnight. The pH was adjusted to about pH 1 by adding 1N HCl and then the mixture was diluted with water and extracted into ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated to give 335.7 mg (94% yield) of the product as a white solid. 1H NMR (CDCl3) δ 2.37-2.57 (m, 2H); 3.21-3.31 (m, 1H); 4.01 (q, 1H, J=8.6); 4.33 (d, 1H, J=13.7); 4.44 (d, 1H, J=13.7); 4.98 (dd, 1H, J=9.4, 8.6); 7.34-7.53 (series of m, 5H).

Workup

  1. temperatureThe mixture was warmed to about room temperature
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93462b368236437f925087cde1fdcabb
Source dataset
uspto-grants-2003_04
Patent number
US06544976B1

Reaction notes

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