Tert-Butylamine → Methyl 5-[(tert-butylamino)sulfonyl]-2-furoate

HRID 2388793Notes

Reaction equation

HRID 2388793 reaction equation
Cl[S:2]([C:5]1[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:14]([NH:18][S:2]([C:5]1[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 2736845Methyl 5-(Chlorosulfonyl)-2-Furoate

Product 1

HCID 67051246Methyl 5-[(tert-butylamino)sulfonyl]-2-furoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-(chlorosulfonyl)-2-furoate (3.0 g) in DCM (100 mL) was added tert-butylamine (3.6 mL). After stirring at room temperature for 2 days the mixture was filtered through a pad of celite, washing with DCM (2×10 mL). The filtrate was evaporated to dryness in vacuo. The resulting crude residue was purified by column chromatography using EtOAc/isohexane (2:8) as eluent to give the subtitle compound as a foam Yield: 2.75 g.

Workup

  1. filtrationwas filtered through a pad of celite
  2. washwashing with DCM (2×10 mL)
  3. customThe filtrate was evaporated to dryness in vacuo
  4. customThe resulting crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-dc14b9b4362b4bacbc2578890b0c4522
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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