Hydrochloric Acid → 4-Trifluoromethanesulfonylamino-butyryl chloride

HRID 2216134Notes

Reaction equation

HRID 2216134 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]([F:14])([F:13])[F:12])(=[O:10])=[O:9].[OH-].[Na+].Cl.S(Cl)([Cl:21])=O>CO.ClCCl.CN(C=O)C>[F:12][C:11]([F:14])([F:13])[S:8]([NH:7][CH2:6][CH2:5][CH2:4][C:3]([Cl:21])=[O:2])(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 866011824-Trifluoromethanesulfonylamino-butyric acid methyl ester

Product 1

HCID 218861334-Trifluoromethanesulfonylamino-butyryl chloride

Reagents, catalysts & solvents 2

HCID 22350042dichloromethane N,N-dimethylformamideCatalystHCID 887MethanolSolvent

Procedure

4-Trifluoromethanesulfonylamino-butyric acid methyl ester (0.42 g, 1.77 mmol) [example 212, step a] was taken up in methanol [2 mL] and 1N NaOH was added [2.66 mL] and stirred for 2 hours. 1N HCl was added and the product was extracted with ethyl acetate, dried with magnesium sulfate and evaporated. The crude product (0.13 g, 0.57 mmol) was dissolved in dichloromethane/DMF [1 mL/1 drop] and thionyl chloride (0.08 mL, 1.14 was added. The reaction was stirred at room temperature for 2 hours and then evaporated and used directly in the next step.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialdried with magnesium sulfate
  3. customevaporated
  4. stirringThe reaction was stirred at room temperature for 2 hours
  5. customevaporated

Sources & evidence

ORD record
ord-e573fb40a0fa4892bf12d366646aedc7
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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