Sodium hydroxide ethanol → N-{2-[3-(3-Benzyl-azetidin-3-yl)-phenoxy]-ethyl}-C-cyclopropyl-methane sulfonamide

HRID 331700

Reaction equation

HRID 331700 reaction equation
C(OC([N:6]1[CH2:9][C:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH:24]3[CH2:26][CH2:25]3)(=[O:22])=[O:21])[CH:11]=2)[CH2:7]1)=O)C.[OH-].[Na+].CCO>[Cl-].[Na+].O>[CH2:27]([C:8]1([C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[O:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH:24]2[CH2:25][CH2:26]2)(=[O:22])=[O:21])[CH2:7][NH:6][CH2:9]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 23692425Sodium hydroxide ethanolHCID 667467573-Benzyl-3-[3-(2-cyclopropylmethanesulfonylamino-ethoxy)-phenyl]-azetidine-1-carboxylic acid ethyl ester

Product 1

HCID 66746666N-{2-[3-(3-Benzyl-azetidin-3-yl)-phenoxy]-ethyl}-C-cyclopropyl-methane sulfonamide

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To 3-benzyl-3-[3-(2-cyclopropylmethanesulfonylamino-ethoxy)-phenyl]-azetidine-1-carboxylic acid ethyl ester (50 mg, 0.11 mmol) was added 4 ml 2N NaOH/EtOH. The mixture was heated for 1 hour in a microwave. After cooling to room temperature 50% brine was added and the mixture extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium bicarbonate, filtered and the solvent evaporated. The residue was purified on 4 g SiO2 using 10% methanol in dichloromethane affording the desired product as a clear oil. m=15.5 mg

Workup

  1. temperatureThe mixture was heated for 1 hour in a microwave
  2. additionwas added
  3. extractionthe mixture extracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium bicarbonate
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified on 4 g SiO2 using 10% methanol in dichloromethane affording the desired product as a clear oil

Sources & evidence

ORD record
ord-b45ddf19bd5e48ad84259f297dd38baa
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Linked notes

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