Benzenesulfonyl chloride → HCID 86590379, compound

HRID 2119414Notes

Reaction equation

HRID 2119414 reaction equation
[CH3:1][C:2]1([C:7]2([C:10]3[CH:15]=[CH:14][C:13]([C@@:16]4([CH2:22][OH:23])[O:20][C:19](=[O:21])[NH:18][CH2:17]4)=[CH:12][CH:11]=3)[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4][O:3]1.C(N(CC)CC)C.[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH3:1][C:2]1([C:7]2([C:10]3[CH:11]=[CH:12][C:13]([C@@:16]4([CH2:22][O:23][S:37]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)(=[O:39])=[O:38])[O:20][C:19](=[O:21])[NH:18][CH2:17]4)=[CH:14][CH:15]=3)[CH2:9][CH2:8]2)[O:3][CH2:4][CH2:5][O:6]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 69842580HCID 69842580, compound

Product 1

HCID 86590379HCID 86590379, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5(R)-[4-(1-(2-methyl-1,3-dioxolan-2-yl)cyclopropan-1-yl)phenyl]-5-hydroxymethyloxazolidin-2-one (2.55 g) and triethylamine (1.7 mL) in tetrahydrofuran (20 mL) was added benzenesulfonyl chloride (1.2 mL) at 0° C., the mixture was stirred at room temperature overnight, and heated at 40° C. for 10 hours. After dilution with water, the mixture was extracted with tetrahydrofuran. The organic extracts were washed with 1 N hydrochloric acid, saturated sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=1:1) of the residue gave 5(R)-[4-(1-(2-methyl-1,3-dioxolan-2-yl)cyclopropan-1-yl)phenyl]-5-phenylsulfonyloxymethyloxazolidin-2-one (3.05 g).

Workup

  1. temperatureheated at 40° C. for 10 hours
  2. extractionAfter dilution with water, the mixture was extracted with tetrahydrofuran
  3. washThe organic extracts were washed with 1 N hydrochloric acid, saturated sodium hydrogencarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f147991bd134a73bd4cb1ec501ec757
Source dataset
uspto-grants-2004_02
Patent number
US06686363B2

Reaction notes

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