Methyl chloroformate → HCID 86599588, compound

HRID 1174400Notes

Reaction equation

HRID 1174400 reaction equation
[NH2:1][CH:2]([CH2:6][NH:7][C:8]([NH2:10])=[O:9])[C:3]([OH:5])=[O:4].Cl[C:12]([O:14][CH3:15])=[O:13]>O1CCOCC1.[OH-].[Na+]>[NH2:10][C:8]([NH:7][CH2:6][C@@H:2]([C:3]([OH:5])=[O:4])[NH:1][C:12]([O:14][CH3:15])=[O:13])=[O:9]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 3481531483-07-4

Product 1

HCID 86599588HCID 86599588, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-amino-3-ureido-propionic acid (0.147 g, 1.0 mmol) in 1,4-dioxane (1.0 mL) and 1 N NaOH (3.6 mL) was treated with methyl chloroformate (0.153 mL, 2.0 mmol), stirred at 60° C. for 7 hours, and extracted with dichloromethane. The aqueous phase was acidified to pH 7 with 1 N HCl and evaporated to dryness. The resulting solid was trituated with 3:1 dichloromethane/isopropanol, filtered, and the filtrate was concentrated to yield a white solid (0.11 g, 53.6%) which was used for the next step without further purification.

Workup

  1. extractionextracted with dichloromethane
  2. customevaporated to dryness
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e49373e729804b24b55ac4a1eadc0c18
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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