Hydrochloric Acid → HCID 11704142, compound

HRID 853124Notes

Reaction equation

HRID 853124 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>CN(C=O)C.CCOCC>[F:10][C:9]([F:11])([F:12])[C:8]([CH:5]1[CH2:4][CH2:3][CH:2]([NH:1][S:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:35])=[O:34])[CH2:7][CH2:6]1)([OH:17])[C:13]([F:14])([F:15])[F:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86605616HCID 86605616, compound

Product 1

HCID 11704142HCID 11704142, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg (0.37 mmol) of the acetate salt of 2-(4-amino-cyclohexyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol in 5 mL of DMF was treated with 0.2 mL (1.16 mmol) of DIPEA and 0.144 mL (1.1 mmol) of benzenesulfonyl chloride. The mixture was stirred for 1 hr and distributed between a diluted aqueous solution of HCl and Et2O. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. Column chromatography on silica gel with EtOAc/heptane 1:1 gave 90 mg (72%) of N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-benzenesulfonamide as a pink solid, MS: 404 (M−H)−.

Workup

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cc49b2fbc7d744af85250a32f9ce916c
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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