Hydrochloric Acid → 4-Trifluoromethanesulfonylamino-butyric acid methyl ester

HRID 2216133Notes

Reaction equation

HRID 2216133 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3](Cl)(=[O:5])=[O:4].Cl.[CH3:10][O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][NH2:16].C(N(CC)CC)C.Cl>ClCCl>[CH3:10][O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][NH:16][S:3]([C:2]([F:8])([F:7])[F:1])(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 27563834-Aminobutyric acid methyl ester hydrochloride

Product 1

HCID 866011824-Trifluoromethanesulfonylamino-butyric acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonyl chloride (0.23 mL, 2.16 mmol) was added dropwise to a solution of 4-amino-butyric acid methyl ester hydrochloride (0.30 g, 1.96 mmol) and triethylamine (0.68 mL, 4.90 mmol) in dichloromethane and stirred at room temperature for 18 hours. 1N HCl was added and the product was extracted with dichloromethane, dried with magnesium sulfate and evaporated to give the title compound (0.42 g, 85%). 1H-NMR (CDCl3): δ 4.89 (s, 1H), 3.12 (t, 2H, J=7.2 Hz), 2.94 (s, 3H), 2.41 (t, 2H, J=7.2 Hz), 1.84 (m, 2H, J=7.2 Hz).

Workup

  1. extractionthe product was extracted with dichloromethane
  2. dry with materialdried with magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-5e528226777e4625bf0ea89b44291a54
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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