Beta-Alanine → N-Benzyloxycarbonyl-beta-alanine

HRID 1722900Notes

Reaction equation

HRID 1722900 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[CH2:9]([O:16][C:17](Cl)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([O:16][C:17]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 239Beta-AlanineHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 75313N-Benzyloxycarbonyl-beta-alanine

Procedure

To a solution of 3.0 g of β-alanine in 37 ml of a 2N-aqueous sodium hydroxide solution was added 5.8 ml of benzyloxycarbonyl chloride under ice-cooling, and then the mixture was stirred for 30 minutes. The reaction mixture was washed with diethyl ether, adjusted to a pH of 2-3 by adding a 1N-hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 6.53 g of N-benzyloxycarbonyl-β-alanine as a white powder.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with diethyl ether
  3. additionby adding a 1N-hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-592f4d18f5384e7c92583cd596fe6fd5
Source dataset
uspto-grants-1989_08
Patent number
US04857650

Reaction notes

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