1,2-Dichloroethane → HCID 178505136, compound

HRID 585705Notes

Reaction equation

HRID 585705 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si](C(C)(C)C)(C)C)[CH:12]=[CH:11][C:10]=1[C@H:23]1[CH2:28][CH2:27][C@H:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH2:25][CH2:24]1)(C(C)(C)C)(C)C.ClCCCl.FC(F)(F)C(O)=O.O>C1(C)C=CC=CC=1>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[C@H:23]1[CH2:24][CH2:25][C@H:26]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 6422Trifluoroacetic acidHCID 178455057HCID 178455057, compound

Product 1

HCID 178505136HCID 178505136, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added trans-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]methanesulfonamide (320 mg, 0.57 mmol) and 1,2-dichloroethane (50 ml). To the stirred solution was added trifluoroacetic acid (20 ml) and water (20 ml). The stirred reaction mixture was then heated under reflux for 18 hr and then cooled to room temperature. Toluene (70 ml) was added and the solvent removed in vacuo. Methanol (50 ml) was then added to the residue and the solvent removed under reduced pressure. The resulting oil was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:3, 1:2, then 1:1 v/v) to furnish the title product (115 mg, 71%) as a white solid. m/z (ES+) 286 (M+H+); δH(CD3OD) 1.52 (4H, m), 1.89 (2H, m), 2.13 (2H, m), 2.80 (1H, m), 3.00 (3H, s), 3.28 (1H, m), 6.27 (1H, d), 6.29 (1H, dd), 6.92 (1H, d).

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. customThe stirred reaction mixture
  3. temperaturewas then heated
  4. temperatureunder reflux for 18 hr
  5. customthe solvent removed in vacuo
  6. additionMethanol (50 ml) was then added to the residue
  7. customthe solvent removed under reduced pressure
  8. customThe resulting oil was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:3, 1:2

Sources & evidence

ORD record
ord-0facb9c2487f43c8ae9f10e7ed96e83f
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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