Chloroacetyl chloride → HCID 43700001, compound

HRID 1770733Notes

Reaction equation

HRID 1770733 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C:5]([NH2:8])([CH3:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+].[Cl:16][CH2:17][C:18](Cl)=[O:19]>C(OCC)(=O)C.O>[Cl:16][CH2:17][C:18]([NH:8][C:5]([CH3:7])([CH3:6])[C:4]([O:3][CH3:2])=[O:9])=[O:19]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 43700001HCID 43700001, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a rapidly stirring biphasic solution of aminoisobutyric acid methyl ester hydrochloride (5.1 g, 33 mmol) in ethyl acetate (40 mL) and water (27 mL) was added potassium carbonate (13.7 g, 99.6 mmol) followed by chloroacetyl chloride (3.4 mL, 43 mmol). The reaction was cooled with an ice bath to prevent warming above ambient temperature, and stirred at room temperature for four hours. The mixture was diluted with ethyl acetate and the organic layer was successively washed with 10% citric acid and sat. NaCl, dried over sodium sulfate and concentrated in vacuo to give the desired product as a white solid (5.78 g, 29.9 mmol, 91%). 1H NMR (CDCl3, 400 MHz) δ 1.61 (s, 6H), 3.78 (s, 3H), 4.01 (s, 2H); LRMS (ESI/APCI) m/z 194 [M+H]+.

Workup

  1. temperatureThe reaction was cooled with an ice bath
  2. temperatureto prevent warming above ambient temperature
  3. washthe organic layer was successively washed with 10% citric acid and sat. NaCl
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-340fe8d498144fc18ae52c79bc404fd5
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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