Methyl chloroformate → HCID 59166438, compound

HRID 1174402Notes

Reaction equation

HRID 1174402 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[C:3]([OH:5])=[O:4].Cl[C:14]([O:16][CH3:17])=[O:15]>O1CCOCC1.[OH-].[Na+]>[CH3:17][O:16][C:14]([NH:1][C@H:2]([C:3]([OH:5])=[O:4])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:15]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 42104063-Pyridin-2-yl-L-alanine

Product 1

HCID 59166438HCID 59166438, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-amino-3-pyridin-2-yl-propionic acid (0.168 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 yellow solid (0.146 g, 65%) 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-2313a1cb47404fb789d8e40de042635f
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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