Chloroacetic Acid → HCID 43700001, compound

HRID 2062078Notes

Reaction equation

HRID 2062078 reaction equation
[Cl:1][CH2:2][C:3](O)=[O:4].[CH3:6][O:7][C:8](=[O:13])[C:9]([NH2:12])([CH3:11])[CH3:10].C(N(CC)C(C)C)(C)C>C1COCC1>[CH3:6][O:7][C:8](=[O:13])[C:9]([NH:12][C:3](=[O:4])[CH2:2][Cl:1])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 81531DiisopropylethylamineHCID 4186341Methyl 2-amino-2-methylpropanoate

Product 1

HCID 43700001HCID 43700001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.95 g chloro acetic acid in 20 ml of dry THF 1.78 g N,N′-carbonyl-diimidazole were added. After 0.5 h at room temperature and under argon atmosphere 1.69 g 2-amino-2-methyl-propionic acid methyl ester and 1.29 g N,N-diisopropyl-ethyl-amine were added and it was stirred for 3 h. Then the solvent was evaporated, the residue taken up in ethyl acetate and washed with 2 M hydrochloric acid, water and sat. aqueous sodium hydrogen carbonate solution. The combined organic fractions were dried over sodium sulphate, filtrated and concentrated. The resulting residue was crystallized from diethylether to yield 2-(2-chloro-acetylamino)-2-methyl-propionic acid methyl ester.

Workup

  1. customThen the solvent was evaporated
  2. washwashed with 2 M hydrochloric acid, water and sat. aqueous sodium hydrogen carbonate solution
  3. dry with materialThe combined organic fractions were dried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. customThe resulting residue was crystallized from diethylether

Sources & evidence

ORD record
ord-aaffaad8fc7f4287a35f12dfdfab8013
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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