Methanesulfonyl chloride → HCID 86681661, compound

HRID 571247Notes

Reaction equation

HRID 571247 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[N:6]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:5]2=[O:19].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:12][O:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[C:5](=[O:19])[N:6]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]2=[O:13]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 86681660HCID 86681660, compound

Product 1

HCID 86681661HCID 86681661, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 2-(5-amino-6-methoxy-1,3-dioxoisoindolin-2-yl)acetate (0.202 g, 0.764 mmol) in pyridine (10 ml) was cooled to 0° C., and methanesulfonyl chloride (0.071 ml, 0.917 mmol) was added. The mixture was warmed to room temperature and stirred for 1 hour. Additional methanesulfonyl chloride (0.090 ml, 1.146 mmol) was added over 30 hour, cooling to 0° C. and stirring at room temperature. The solvent was removed under vacuum, and the crude was partitioned between ethyl acetate and 1N HCl. The organic phase was washed with brine and dried over sodium sulfate. The solvent was removed and the crude was purified by chromatography on silica gel cartridge (petroleum ether:ethyl acetate from 6:4 to 100% ethyl acetate) affording methyl 2-(5-methoxy-6-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (0.200 g, 0.584 mmol, 76% yield). MS/ESI+ 342.9 [MH]+.

Workup

  1. temperaturecooling to 0° C.
  2. stirringstirring at room temperature
  3. customThe solvent was removed under vacuum
  4. customthe crude was partitioned between ethyl acetate and 1N HCl
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed
  8. customthe crude was purified by chromatography on silica gel cartridge (petroleum ether:ethyl acetate from 6:4 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-a646af482f3d419b90e3ae69ff113a5e
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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