Triethylamine → Tert-butyl {[methyl(tetrahydrofuran-3-yl)amino]sulfonyl}carbamate

HRID 222281Notes

Reaction equation

HRID 222281 reaction equation
[C:1]([O:5][C:6]([N-:8][S:9]([N:12]1[CH:17]=C[C:15](=[N+](C)C)[CH:14]=[CH:13]1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].C[NH2+]C1CC[O:26][CH2:25]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:17][N:12]([CH:13]1[CH2:14][CH2:15][O:26][CH2:25]1)[S:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67365389N-methyltetrahydrofuran-3-aminium chlorideHCID 178482962HCID 178482962, compound

Product 1

HCID 86609783Tert-butyl {[methyl(tetrahydrofuran-3-yl)amino]sulfonyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask was charged with N-tert-butoxycarbonyl-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (2.19 g, 7.27 mmol), N-methyltetrahydrofuran-3-aminium chloride (1.00 g, 7.27 mmol) and triethyl amine (1.01 mL, 7.27 mmol) in 10 mL of CH2Cl2. After 2 h, the solution was concentrated in vacuo and purified by flash column chromatography (10-100% EtOAc/hexanes) to afford tert-butyl {[methyl(tetrahydrofuran-3-yl)amino]sulfonyl}carbamate.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by flash column chromatography (10-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a21c566733604deb83b6622208ee73a5
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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