Potassium Carbonate → HCID 22476595, compound

HRID 2184403Notes

Reaction equation

HRID 2184403 reaction equation
[OH:1][C:2]1([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].Br[CH2:22][C:23]#[N:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][C:2]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:22][C:23]#[N:24])=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 9922336HCID 9922336, compound

Product 1

HCID 22476595HCID 22476595, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

[2-Hydroxy-2-(4-hydroxyphenyl)cyclopentyl][(methylethyl)sulfonyl]amine (650 mg, 2.17 mmol, prepared in example 47), bromoacetonitrile (292 mg, 1.1 eq), and potassium carbonate (360 mg, 1.2 eq) were combined with acetone (40 mL) and stirred overnight at room temperature under a nitrogen atmosphere. The solution was then filtered and the filtrate was concentrated under reduced vacuum to yield 694 mg as an oil. This two spot 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 9:1 to yield the intermediate title compound (390 mg, 54%) as a white foam (top spot by TLC). Ion Spray M.S. 337.2 (M*−1) Calculated for C16H22N2O4S: Theory: C, 56.79; H, 6.55; N, 8.28. Found: C, 56.51; H, 6.46; N, 8.24.

Workup

  1. filtrationThe solution was then filtered
  2. concentrationthe filtrate was concentrated under reduced vacuum
  3. customto yield 694 mg as an oil
  4. customThis two spot material was separated
  5. custompurified via silica gel chromatography
  6. washwhile eluting with a solvent of methylene chloride/ethyl acetate 9:1

Sources & evidence

ORD record
ord-1e3d8f62bad944fa96e350d3872eba6d
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

Loading…