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

HRID 480364Notes

Reaction equation

HRID 480364 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 chloride2×HCID 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 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(3-amino-propyl)-furan-2-carboxylic acid methyl ester hydrochloride salt (see Preparation DD2) (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) in CH2Cl2 (15 mL) at 0° C. was added methanesulfonyl chloride (86 mg, 0.75 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. washwas 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-fa3d93d8d99f4ed48918c9adba9de8e4
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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