Hydrochloric Acid → 4-[(Methoxycarbonyl)(methyl)amino]butanoic acid

HRID 459049Notes

Reaction equation

HRID 459049 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]([O:19][CH3:20])=[O:18].Cl>O.O1CCOCC1>[CH3:20][O:19][C:17]([N:3]([CH3:2])[CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 126266544-(Methylamino)butyric acid hydrochloride

Product 1

HCID 184429704-[(Methoxycarbonyl)(methyl)amino]butanoic acidYield 170.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

4-(Methylamino)butyric acid hydrochloride (5 g, 32.5 mmol), and potassium carbonate (18 g, 130 mmol) were suspended in water (50 ml) and dioxane (25 ml) then cooled to 0° C. Methyl chloroformate (13 ml, 168 mmol) was added over 1 minute, then the mixture was stirred and allowed to warm slowly to room temperature for 16 hours. Conc. HCl (20 ml) was added then the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, evaporated and dried in vacuo to give 4-[(methoxycarbonyl)(methyl)amino]butyric acid as a thick clear oil (9.7 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-17349bdd874948b3a3394414256d671c
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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