Methanol → Methyl (2S)-azetidine-2-carboxylate--hydrogen chloride (1/1)

HRID 479628Notes

Reaction equation

HRID 479628 reaction equation
[NH:1]1[CH2:4][CH2:3][C@H:2]1[C:5]([OH:7])=[O:6].S(Cl)([Cl:10])=O.[CH3:12]O>>[ClH:10].[NH:1]1[CH2:4][CH2:3][C@H:2]1[C:5]([O:7][CH3:12])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 16486L-Azetidine-2-carboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 13246224Methyl (2S)-azetidine-2-carboxylate--hydrogen chloride (1/1)Yield 96%

Procedure

To a suspension of azetidine-2(S)-carboxylic acid (19.8 mmol, 2.0 g) in methanol (120 mL) at 0° C. was added thionyl chloride (4.0 equiv; 79.2 mmol, 9.43 g, 5.8 mL) dropwise. Dissolution was observed during the addition and the reaction mixture was stirred at ambient temperature overnight (20 h). After this time, solvent was evaporated and the oily residue was azeotroped with toluene and placed under high vacuum to give rise to azetidine-2(S)-carboxylic acid, methyl ester hydrochloride salt as an off-white solid (2.9 g, 96% yield).

Workup

  1. dissolutionDissolution
  2. additionwas observed during the addition
  3. customAfter this time, solvent was evaporated
  4. customthe oily residue was azeotroped with toluene

Sources & evidence

ORD record
ord-0262ada685a6442fa97b39ee789ffb5b
Source dataset
uspto-grants-2003_11
Patent number
US06645939B1

Reaction notes

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