4-Toluenesulfonyl chloride → HCID 71623076, compound

HRID 1048852Notes

Reaction equation

HRID 1048852 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][NH:7][C:6](=[O:9])[CH2:5][O:4]1.C(N(CC)CC)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>ClCCl>[CH3:24][C:23]1[CH:25]=[CH:26][C:20]([S:17]([O:1][CH2:2][CH:3]2[O:4][CH2:5][C:6](=[O:9])[NH:7][CH2:8]2)(=[O:19])=[O:18])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 534019466-(Hydroxymethyl)morpholin-3-one

Product 1

HCID 71623076HCID 71623076, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 6-(hydroxymethyl)morpholin-3-one (Step-2 of Intermediate-9) (4.1 g, 31.29 mmole) in dichloromethane (25 mL), triethylamine (8.31 mL, 62.59 mmole) and TsCl (tosyl chloride) (6.56 g, 34.42 mmole) were added at 0° C. The reaction mixture was allowed to RT and further stirred overnight. Reaction mixture was diluted with dichloromethane (30 mL), and washed with brine solution (2×30 mL) and DM water, separated the organic layer, dried over Na2SO4, concentrated and further purified by flash chromatography (n-hexane:ethyl acetate, 1:4) to get the title compound as a white solid (3.8 gm). m/z 286.1

Workup

  1. customReaction mixture
  2. washwashed with brine solution (2×30 mL) and DM water
  3. customseparated the organic layer
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customfurther purified by flash chromatography (n-hexane:ethyl acetate, 1:4)

Sources & evidence

ORD record
ord-019df83d78ad441490b6650d762c9d3e
Source dataset
uspto-grants-2016_07
Patent number
US09382216B2

Reaction notes

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