Beta-Alanine → N-Benzyloxycarbonyl-beta-alanine

HRID 1982336Notes

Reaction equation

HRID 1982336 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:7]([O:14][C:15](Cl)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[OH-].[Na+].C1(C)C=CC=CC=1>[NH:1]([C:15]([O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:16])[CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 239Beta-AlanineHCID 10387Benzyl chloroformate

Product 1

HCID 75313N-Benzyloxycarbonyl-beta-alanine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

6.0 g of β-alanine are taken up in 33.7 ml of 2N NaOH and cooled to +5°. At this temperature there are then added dropwise, simultaneously, 22.5 ml of a 50% solution of chloroformic acid benzyl ester in toluene and 16.8 ml of 4N NaOH. The emulsion is subsequently stirred in an ice bath for 3 hours. After separating off the organic phase, the aqueous phase is extracted once more with ether and then, while cooling with an ice bath, the pH is adjusted to 1 with 44 ml of 2N HCl. By filterirg off the precipitate and drying in a high vacuum at 50°, Z-β-Ala-OH is obtained in the form of a white powder; Rf (CH2Cl2 /MeOH/concentrated aqueous ammonia solution [5:3:1])=0.37.

Workup

  1. temperaturecooled to +5°
  2. additionAt this temperature there are then added dropwise
  3. customAfter separating off the organic phase
  4. extractionthe aqueous phase is extracted once more with ether
  5. temperaturewhile cooling with an ice bath
  6. customdrying in a high vacuum at 50°

Sources & evidence

ORD record
ord-2bab1d00b2d9477d974a9b7cde435d15
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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