Triethylamine → (4-Fluorosulfonyl-benzoylamino)-acetic acid tert-butyl ester

HRID 382040Notes

Reaction equation

HRID 382040 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].CCN(CC)CC.[F:18][S:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>CN(C)C=O.C(OCC)(=O)C>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([S:19]([F:18])(=[O:21])=[O:20])=[CH:23][CH:24]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 976284-(Fluorosulfonyl)benzoyl chlorideHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 53723910(4-Fluorosulfonyl-benzoylamino)-acetic acid tert-butyl esterYield 95.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of glycine tert-butyl ester hydrochloride (300 mg, 1.79 mmol) (Aldrich), Et3N (250 μL, 1.79 mmol), and 4-(fluorosulfonyl)benzoyl chloride (400 mg, 1.79 mmol) (Aldrich) in 9 mL of dry N,N-dimethylformamide was stirred at room temperature under a nitrogen atmosphere for 12 h. The reaction mixture was diluted with ethyl acetate. The organic phase was washed with distilled water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude (4-fluorosulfonyl-benzoylamino)-acetic acid tert-butyl ester (541 mg, 95%) as an oil that solidified upon sitting at room temperature. The crude (4-fluorosulfonyl-benzoylamino)-acetic acid tert-butyl ester was used without further purification.

Workup

  1. washThe organic phase was washed with distilled water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-962be8bd57974e4ca737ff26e0c7293f
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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