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

HRID 591198Notes

Reaction equation

HRID 591198 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-ea9e48ff91af44a58f628cd18639c23c
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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