Hydrochloric Acid → HCID 178484815, compound

HRID 2118235Notes

Reaction equation

HRID 2118235 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.Cl.C[Si](C)(C)N[Si](C)(C)C.[F:22][C:23]([F:35])([F:34])[C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.[OH-].[Na+].Cl>O>[CH3:1][N:2]([S:30]([C:27]1[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:34])[F:35])=[CH:29][CH:28]=1)(=[O:32])=[O:31])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 14798Sodium HydroxideHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 178484814HCID 178484814, compound

Product 1

HCID 178484815HCID 178484815, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

0.194 g (1.00 mmol) of trans-4-methylamino-cyclohexanecarboxylic acid•HCl were mixed with 2.62 mL (12.58 mmol, 12.6 eq) of hexamethyldisilazane and heated under reflux to 140° C. for 1 h (total time 1.5 h). The solution was evaporated, suspended in THF and treated with 0.245 g (1.00 mmol, 1 eq) of 4-(trifluoromethyl)-benzenesulfonyl chloride at 0° C. and stirred at RT overnight. 1 mL of water was added at RT followed by 2 mL of 1M NaOH. Stirring was continued for 1 h at RT after this aqueous 1M HCl was added. The solution was then partitioned between Et2O (×3)/H2O, dried over Na2SO4 and evaporated to yield 0.234 g (64%) of trans-4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexanecarboxylic acid, MS: 364 (M−H−).

Workup

  1. temperatureheated
  2. customThe solution was evaporated
  3. stirringStirring
  4. waitwas continued for 1 h at RT
  5. customThe solution was then partitioned between Et2O (×3)/H2O
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-32bdb00ebdc34117b028352ebda3895b
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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