Ammonium Chloride → HCID 178477575, compound

HRID 853137Notes

Reaction equation

HRID 853137 reaction equation
[CH2:1]([S:8]([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:27][Si:28]([CH2:33][CH3:34])([CH2:31][CH3:32])[CH2:29][CH3:30])([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])[CH2:14][CH2:13]1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li].C[Si]([N-][Si](C)(C)C)(C)C.[F:45][C:46]([F:57])([F:56])[CH2:47]OS(C(F)(F)F)(=O)=O.[NH4+].[Cl-]>C1COCC1.CCOCC>[CH2:1]([S:8]([N:11]([CH2:47][C:46]([F:57])([F:56])[F:45])[C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:27][Si:28]([CH2:31][CH3:32])([CH2:33][CH3:34])[CH2:29][CH3:30])([C:23]([F:24])([F:25])[F:26])[C:19]([F:20])([F:21])[F:22])[CH2:14][CH2:13]1)(=[O:10])=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 86605622Lithium bistrimethylsilylamideHCID 178477579HCID 178477579, compound

Product 1

HCID 178477575HCID 178477575, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of 200 mg (0.37 mmol) of trans benzyl-N-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-sulfonamide (example 29.1) in 2 mL of THF was cooled to −78° C. and treated dropwise with a 0.4 mL of a 1M lithium-bis-(trimethylsilyl)amide-solution in THF. The mixture was warmed to −40° C., treated with 609 mg (2.6 mmol) of trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester and allowed to reach RT. After 4 hours of refluxing, the mixture was cooled to RT and distributed between a saturated aqueous solution of NH4Cl and Et2O. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. Chromatography on silica gel with heptane/EtOAc 9:1 gave 140 mg (61%) of trans benzyl-N-(2,2,2-trifluoro-ethyl)-N-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-sulfonamide as a light yellow oil, MS: 614 (M−H)−.

Workup

  1. customto reach RT
  2. temperatureAfter 4 hours of refluxing
  3. temperaturethe mixture was cooled to RT
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a4cd39d9ac434b53b2b72dd0d706d2cb
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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