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

HRID 1958972Notes

Reaction equation

HRID 1958972 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-c139c6fbcb6144e3b3906a679a30bdf0
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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