Hydrochloric Acid → (2S)-1-(N-t-butylcarbamoyl)azetidine-2-carboxylic acid

HRID 1264472Notes

Reaction equation

HRID 1264472 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[C:9](=[O:15])[NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:4].[Li+].[OH-].Cl>CO.O>[C:11]([NH:10][C:9]([N:6]1[CH2:7][CH2:8][C@H:5]1[C:3]([OH:4])=[O:2])=[O:15])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59049291HCID 59049291, compound

Product 1

HCID 59049292(2S)-1-(N-t-butylcarbamoyl)azetidine-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of (2S)-methyl-1-(N-t-butylcarbamoyl)azetidine-2-carboxylate from Reference Example 5 (211.6 mg, 0.99 mmol) in methanol (5.0 mL) was added 1N LiOH in water (1.8 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 with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to give 211.3 mg (85% yield) of the product as a yellow oil. 1H NMR (CDCl3) δ 1.38 (s, 9H); 2.34-2.46 (m, 1H); 2.61-2.74 (m, 1H) 3.71-3.88 (m, 2H); 4.18-4.26 (br, 1H); 4.82 (t, 1H, J=8.6).

Workup

  1. customat about 0° C
  2. temperatureThe mixture was warmed to about room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a1c76960a2294b5eb4ad00ed96e9a25b
Source dataset
uspto-grants-2003_04
Patent number
US06544976B1

Reaction notes

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