Triethylamine → 5-(3-Methanesulfonylamino-propyl)-furan-2-carboxylic acid methyl ester

HRID 842737Notes

Reaction equation

HRID 842737 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][CH2:12][CH2:13][NH2:14])=[CH:9][CH:10]=1)=[O:5].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:2][O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][CH2:12][CH2:13][NH:14][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:9][CH:10]=1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 692922505-(3-Amino-propyl)-furan-2-carboxylic acid methyl ester hydrochloride salt

Product 1

HCID 537273525-(3-Methanesulfonylamino-propyl)-furan-2-carboxylic acid methyl esterYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3-amino-propyl)-furan-2-carboxylic acid methyl ester hydrochloride salt (see Preparation 2a) (150 mg, 0.683 mmol), and triethylamine (0.313 mL, 2.25 mmol) in CH2Cl2 (15 mL) at 0° C. was added methanesulfonyl chloride (86 mg, 0.75 mmol). The reaction was stirred at room temperature for 18 h. The organic solution was washed consecutively with dilute HCl, water, saturated NaHCO3, and brine. The organic solution was dried over MgSO4, filtered, and concentrated to provide the title sulfonamide (156 mg). MS 262 (M+1).

Workup

  1. washThe organic solution was washed consecutively with dilute HCl, water, saturated NaHCO3, and brine
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-88b2248e30e6484ebdcee7c11e7fd50f
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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