Water → HCID 66818021, compound

HRID 1755115Notes

Reaction equation

HRID 1755115 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:10][CH2:11][CH2:12][N:13]([CH3:55])[C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][S:24]([N:27]2[CH2:32][CH2:31][C:30]([NH:36][C:37](=O)[C:38]3[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[C:40]([O:48][CH2:49][CH2:50][CH:51]=[CH2:52])[CH:39]=3)([C:33]([NH2:35])=[O:34])[CH2:29][CH2:28]2)(=[O:26])=[O:25])=[C:18]([CH3:54])[CH:17]=1)=[O:15])[CH:8]=[CH2:9].[Cl-].[NH4+].O>C(O)C.[Cl-].[Na+].O>[CH2:7]([O:10][CH2:11][CH2:12][N:13]([CH3:55])[C:14](=[O:15])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][S:24]([N:27]2[CH2:28][CH2:29][C:30]3([N:36]=[C:37]([C:38]4[CH:43]=[CH:42][C:41]([C:44]([F:45])([F:47])[F:46])=[C:40]([O:48][CH2:49][CH2:50][CH:51]=[CH2:52])[CH:39]=4)[NH:35][C:33]3=[O:34])[CH2:31][CH2:32]2)(=[O:26])=[O:25])=[C:18]([CH3:54])[CH:17]=1)[CH:8]=[CH2:9]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 66818366HCID 66818366, compound

Product 1

HCID 66818021HCID 66818021, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

Potassium tert-butoxide (302 mg, 2.69 mmol) was added to a solution of the resulting 1-(2-{4-[(2-allyloxy-ethyl)-methyl-carbamoyl]-2-methyl-phenyl}-ethanesulfonyl)-4-(3-but-3-enyloxy-4-trifluoromethyl-benzoylamino)-piperidine-4-carboxylic amide in ethanol (6 ml), and the mixture was stirred at 80° C. for 30 minutes. A saturated aqueous ammonium chloride solution, water and saturated brine were sequentially added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give N-(2-allyloxy-ethyl)-4-{2-[2-(3-but-3-enyloxy-4-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3,N-dimethyl-benzamide (176 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eefc92c6dd124734ae20edf1e4bca1b5
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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