Ammonium Chloride → HCID 178467851, compound

HRID 25671Notes

Reaction equation

HRID 25671 reaction equation
CON(C)[C:4](=[O:30])[CH2:5][CH2:6][CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([CH3:29])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:11][CH2:10]1.[CH3:32][Mg]Br.[NH4+].[Cl-]>C1COCC1>[CH3:29][N:15]([C@H:12]1[CH2:11][CH2:10][C@H:9]([O:8][CH2:7][CH2:6][CH2:5][C:4](=[O:30])[CH3:32])[CH2:14][CH2:13]1)[S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 178418573HCID 178418573, compoundHCID 178502708HCID 178502708, compound

Product 1

HCID 178467851HCID 178467851, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 260 mg (0.56 mmol) trans-N-Methoxy-N-methyl-4-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-butyramide in 10 ml THF were added 0.56 ml 3M (1.67 mmol, 3 eq) methylmagnesiumbromide in THF at −78° C. The solution was slowly warmed to RT over night, a saturated aqueous solution of NH4Cl was added and the mixture stirred for 30 min. The phases were separated and the inorganic phase was extracted with EtOAc. The combined organic ones were dried over Na2SO4 and evaporated. Column chromatography on silica gel with EtOAc/hexane 1:1 yielded 143 mg (61%) trans-N-Methyl-N-[4-(4-oxo-pentyloxy)-cyclohexyl]-4-trifluoromethyl-benzenesulfonamide as white solid, MS: 422 (MH+).

Workup

  1. customThe phases were separated
  2. extractionthe inorganic phase was extracted with EtOAc
  3. dry with materialThe combined organic ones were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-90ece501a5fc48aba0ae0c2d211eddd4
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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