Methyl chloroformate → HCID 18442964, compound

HRID 459059Notes

Reaction equation

HRID 459059 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([OH:9])=[O:8].C(N(CC)CC)C.[CH3:17][O:18][C:19](Cl)=[O:20]>CN(C=O)C>[CH3:17][O:18][C:19]([N:2]([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][C:7]([OH:9])=[O:8])=[O:20]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 20063809HCID 20063809, compound

Product 1

HCID 18442964HCID 18442964, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[2-(Methylamino)ethoxy]acetic acid (Bull. Soc. Chim.; 1956, 1210) (130 mg, 0.98 mmol) was mixed with triethylamine (0.56 mL, 4 mmol) in dry DMF (2 mL). Methylchloroformate (185 mg, 1.95 mmol) was added and the mixture was stirred at room temperature for 20 minutes, then quenched with water. Aqueous HCl (2M) was added to adjust the pH to ˜2. Product was extracted with ethyl acetate, the organic phase was dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as an oil (100 mg), which was used without further purification.

Workup

  1. customquenched with water
  2. additionAqueous HCl (2M) was added
  3. extractionProduct was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d01136948ac401981350724662e4fa0
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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