Methanesulfonyl chloride → HCID 86681720, compound

HRID 571312Notes

Reaction equation

HRID 571312 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:5]2=[O:23].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH3:24][S:25]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[C:5]2=[O:23])(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86681719HCID 86681719, compound

Product 1

HCID 86681720HCID 86681720, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of benzyl 2-(5-amino-1,3-dioxoisoindolin-2-yl)acetate (1.0 g, 3.22 mmol) in pyridine (8 ml) cooled to 0° C., methanesulfonyl chloride (0.377 ml, 4.83 mmol) was added drop wise, and the resulting mixture was stirred at room temperature for 3 hours. The solvent was removed under vacuum and the residue was partitioned between 2N HCl and DCM; the aqueous phase was extracted with DCM and the combined organic layers were dried over Na2SO4 and evaporated to dryness. The crude was triturated with Et2O (15 ml) to give benzyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (1.1 g, 2.83 mmol, 88% yield, MS/ESI+ 388.8 [MH]+).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between 2N HCl and DCM
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude was triturated with Et2O (15 ml)

Sources & evidence

ORD record
ord-8f7dbaba178641d790cda12a62d179fa
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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