Methanesulfonyl chloride → HCID 86681754, compound

HRID 571337Notes

Reaction equation

HRID 571337 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:7]2=[O:22].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[CH3:23][S:24]([NH:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C:7]2=[O:22])(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 86681752HCID 86681752, compound

Product 1

HCID 86681754HCID 86681754, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl 2-(5-(aminomethyl)-1,3-dioxoisoindolin-2-yl)acetate hydrochloride (0.409 g, 1.252 mmol) in dry pyridine (10 ml) cooled to 0° C., methanesulfonyl chloride (0.117 ml, 1.502 mmol) was added. The reaction was warmed to room temperature and stirred overnight. Additional methanesulfonyl chloride (0.148 ml, 1.878 mmol) was added over 24 hours cooling at 0° C. and stirring at room temperature. The solvent was removed under vacuum and the residue was portioned between ethyl acetate and 1N HCl. The organic phase was washed with brine and dried over sodium sulfate. The solvent was evaporated to dryness affording tert-butyl 2-(5-(methylsulfonamidomethyl)-1,3-dioxoisoindolin-2-yl)acetate (0.461 g, 1.251 mmol, MS/ESI+ 390.9 [MNa]+). This crude was used in the following steps without purification.

Workup

  1. temperaturecooling at 0° C.
  2. stirringstirring at room temperature
  3. customThe solvent was removed under vacuum
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-6a88d16a98ef41cebc84446d48965480
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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