Azetidine → 5-(azetidin-1-ylcarbonyl)-N-(tert-butyl)furan-2-sulfonamide

HRID 1024916Notes

Reaction equation

HRID 1024916 reaction equation
[C:1]([NH:5][S:6]([C:9]1[O:13][C:12]([C:14]([O:16]C)=O)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:18]1[CH2:21][CH2:20][CH2:19]1>CO>[N:18]1([C:14]([C:12]2[O:13][C:9]([S:6]([NH:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:7])=[O:8])=[CH:10][CH:11]=2)=[O:16])[CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 67051246Methyl 5-[(tert-butylamino)sulfonyl]-2-furoate2×

Product 1

HCID 399535195-(azetidin-1-ylcarbonyl)-N-(tert-butyl)furan-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-[(tert-butylamino)sulfonyl]-2-furoate (the product of step i) (2.15 g) in methanol (80 mL) was added azetidine (1.15 mL). After stirring at room temperature for 5 h the mixture was evaporated to dryness in vacuo. The resulting residue was partitioned between EtOAc (50 mL) and H2O (50 mL). The separated organic layer was dried (MgSO4), filtered and evaporated to dryness in vacuo. The resulting crude material was purified by column chromatography (EtOAC as eluent) to give the subtitle compound as a pale yellow oil. Yield: 3 g.

Workup

  1. customwas evaporated to dryness in vacuo
  2. customThe resulting residue was partitioned between EtOAc (50 mL) and H2O (50 mL)
  3. dry with materialThe separated organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. customThe resulting crude material was purified by column chromatography (EtOAC as eluent)

Sources & evidence

ORD record
ord-20275dc60cfa4ca6808e16047d87011f
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

Loading…