Ethyl chloroformate → HCID 15524258, compound

HRID 2303978Notes

Reaction equation

HRID 2303978 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[OH-].[Na+].[NH2:9][CH2:10][CH:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)[CH2:12][C:13]([OH:15])=[O:14]>>[CH2:5]([O:4][C:2]([NH:9][CH2:10][CH:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:3])[CH3:6]

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 15746865HCID 15746865, compound

Product 1

HCID 15524258HCID 15524258, compoundYield 99.9%

Conditions

Temperature
0 °C

Procedure

Ethyl chloroformate (3.19 g, 29.4 mmol) was added to a 2N sodium hydroxide solution (26.3 ml, 52.4 mmol) of 4-amino-3-(3,4-dichlorophenyl)butyric acid (5.61 g, 22.6 mmol) under cooling with ice water and the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 4 hours. The reaction solution was washed with diethyl ether and the aqueous layer was adjusted to a pH of about 2 with 1N hydrochloric acid and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound (7.23 g, quant.) as a light brown oily substance.

Workup

  1. waitat room temperature for 4 hours
  2. washThe reaction solution was washed with diethyl ether
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-519a12d109154a218e0f440815a758b0
Source dataset
uspto-grants-2002_08
Patent number
US06433174B1

Reaction notes

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