(Diethylamino)sulfur trifluoride → HCID 22476585, compound

HRID 2184415Notes

Reaction equation

HRID 2184415 reaction equation
O[C:2]1([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:17][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10].CCN(S(F)(F)[F:35])CC>>[F:35][C:2]1([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:17][CH:16]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10274582HCID 10274582, compound

Product 1

HCID 22476585HCID 22476585, compound

Procedure

The title compound was prepared in a manner analogous to the procedure set forth in Example 59 from [2-hydroxy-2-(4-{2-[(methylsulfonyl)amino]ethoxy}phenyl)cyclohexyl][(methylethyl)sulfonyl]amine (155 mg, 0.36 mmol) and DAST (0.01 mL) to provide a cis/trans mixture of the title compounds (141 mg) as a foam. This material was separated and purified via silica gel chromatography employing the Chromatotron® and using a 4000 micron rotor while eluting with a solvent of methylene chloride/ethyl acetate 4:1 to yield the trans isomer of the title compound (80 mg, top spot by TLC) as a white solid. Ion spray M.S. 435.3 (M*−1) Calculated for C18H29N2O5S2F-½H2O: Theory: C 47.55, H 6.84, N 6.16. Found: C 47.58, H 6.89, N 5.65. Continued elution afforded a cis/trans mixture (61 mg) as a foam. Fd M.S. 435.3 (M*−1). Calculated for C18H29N2O5S2F-½H2O: Theory: C 49.52, H 6.70, N 6.42. Found: C 49.17, H 6.64, N 6.22.

Workup

  1. customThe title compound was prepared in a manner analogous to the procedure
  2. customto provide
  3. customThis material was separated
  4. custompurified via silica gel chromatography
  5. washwhile eluting with a solvent of methylene chloride/ethyl acetate 4:1

Sources & evidence

ORD record
ord-61e102ca63fb4d9d8bdf2439b87379bc
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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