Methanesulfonyl chloride → HCID 86681691, compound

HRID 571283Notes

Reaction equation

HRID 571283 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][CH3:16])=[O:14])[C:5]2=[O:17].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[CH3:18][S:19]([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][CH3:16])=[O:14])[C:5]2=[O:17])(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 28491724HCID 28491724, compound

Product 1

HCID 86681691HCID 86681691, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 2-(5-amino-1,3-dioxoisoindolin-2-yl)acetate (380 mg, 1.622 mmol) in pyridine (10 ml), methanesulfonyl chloride (190 μl, 2.434 mmol) was added, and the mixture was reacted overnight at room temperature. The solvent was evaporated and the resulting crude was partitioned between 1N HCl (10 ml) and EtOAc (10 ml); aqueous phase was extracted with EtOAc (3×20 ml) and the organic phase was dried over sodium sulfate. The solvent was removed affording title compound as a brown solid (550 mg, MS/ESI+ 312.9 [MH]+). It was used in the next step without any additional purification.

Workup

  1. customthe mixture was reacted overnight at room temperature
  2. customThe solvent was evaporated
  3. customthe resulting crude was partitioned between 1N HCl (10 ml) and EtOAc (10 ml)
  4. extractionaqueous phase was extracted with EtOAc (3×20 ml)
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-0e2a9bf1ba574ac79e16a8fe4625bdb6
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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