Beta-Alanine → N-Benzyloxycarbonyl-beta-alanine

HRID 1883302Notes

Reaction equation

HRID 1883302 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]>[OH-].[Na+]>[NH:1]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 239Beta-AlanineHCID 10387Benzyl chloroformate

Product 1

HCID 75313N-Benzyloxycarbonyl-beta-alanineYield 92%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A stirred solution of β-alanine (50.10 g, 0.562 mol) in 2M NaOH (281 mL) at 0° C. was treated with benzyl chloroformate (88 mL, 1.1 equiv), dropwise over 1 h. Stirring was continued for 1.5 h at 0° C., followed by 1.5 h at rt. The resulting mixture was extracted with ether (4×500 mL). The aqueous phase was acidified with 5M HCl (120 mL). The resulting white precipitate was collected by filtration, washed with water and dissolved in methylene chloride. The solution was dried over sodium sulfate and concentrated in vacuo to give a white solid (114.95 g, 92%). 1H-NMR (CDCl3) 6 2.61 (t, 2H), 3.48 (q, 2H), 5.12 (s, 2H), 5.29 (br, 1H), 7.37 (s, 5H). MS (DCl) 224 (MH)+.

Workup

  1. waitfollowed by 1.5 h at rt
  2. extractionThe resulting mixture was extracted with ether (4×500 mL)
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in methylene chloride
  6. dry with materialThe solution was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1768db29f9e4790a6bea723348b009c
Source dataset
uspto-grants-2004_07
Patent number
US06759509B1

Reaction notes

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