Methanesulfonyl chloride → (S)-Glycidyl N-Methylsulfonyl-m-Aminophenyl Ether

HRID 2223427Notes

Reaction equation

HRID 2223427 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@H:10]2[O:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([NH:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@H:10]2[O:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 450910383-{[(2S)-Oxiran-2-yl]methoxy}aniline

Product 1

HCID 86593512(S)-Glycidyl N-Methylsulfonyl-m-Aminophenyl EtherYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 16b-S (0.4 g, 2.4 mmol) dissolved in 20 ml anhydrous DCM, and N,N-diisopropyl-N-ethylamine (0.45 ml, 2.6 mmol) was added at 0° C. After stirring for 15 minutes, methanesulfonyl chloride (0.2 ml, 2.6 mmol) was added to the reaction mixture at 0° C. After stirring overnight, the reaction mixture was extracted with water and washed with brine. The organic phase was dried and evaporated. The residue was purified with flash chromatography using ethyl acetate:DCM (30:70) solvent to give a colorless oil (45% yield).

Workup

  1. stirringAfter stirring overnight
  2. extractionthe reaction mixture was extracted with water
  3. washwashed with brine
  4. customThe organic phase was dried
  5. customevaporated
  6. customThe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-12f0b312c30941e8b6fdd8ccbb1b09c0
Source dataset
uspto-grants-2008_05
Patent number
US07375136B2

Reaction notes

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