Hydrochloric Acid → HCID 131722849, compound

HRID 1596092Notes

Reaction equation

HRID 1596092 reaction equation
C1(C([O:20][CH2:21][CH2:22][C@H:23]2[O:27][C:26](=[O:28])[N:25]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:24]2[C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.C(N(CC)CC)C.[CH3:52][S:53](Cl)(=[O:55])=[O:54]>O1CCOCC1.C(Cl)Cl>[CH3:52][S:53]([O:20][CH2:21][CH2:22][C@H:23]1[O:27][C:26](=[O:28])[N:25]([CH2:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:24]1[C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=1)(=[O:55])=[O:54]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131722850HCID 131722850, compound

Product 1

HCID 131722849HCID 131722849, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

An alcohol derivative (930 mg, 91%) was prepared according to the procedures described in Example 12(d) using 2-[3-(cyclohexylmethyl)-(5R)-(3,4-dichlorophenyl)-2-oxooxazolidin-5-yl]ethanol triphenylmethylether (1.69 g, 2.75 mmol) and a solution of hydrogen chloride in dioxane (4N, 6.9 ml). The alcohol derivative (880 mg, 2.36 mmol) was dissolved in methylene chloride (18 ml), and triethylamine (0.50 ml, 3.55 mmol) and methanesulfonyl chloride (0.22 ml, 2.84 mmol) were added to the solution. The mixture was stirred at room temperature overnight. To the reaction mixture, methylene chloride was added, and this was washed with water and then with a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by flash chromatography on a silica gel column using n-hexane/ethyl acetate=4/1−1/1 as an eluant to afford the title compound (1.03 g, 97%).

Workup

  1. washthis was washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-e941843a1fd34575b48c1f1c19eacfe2
Source dataset
uspto-grants-2001_09
Patent number
US06288059B1

Reaction notes

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