Beta-Alanine → N-(butoxycarbonyl)-beta-alanine

HRID 1591773Notes

Reaction equation

HRID 1591773 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].Cl[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11].Cl>CCC(C)C>[CH2:13]([O:12][C:10]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:11])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 61140Butyl chloroformate

Product 1

HCID 19736008N-(butoxycarbonyl)-beta-alanineYield 68%

Reagents, catalysts & solvents 1

HCID 6556IsopentaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution containing β-alanine (8.9 g; 0.1 mol) and 100 ml of a 1N solution of sodium hydroxide is cooled down to 10° C. n-butyl chloroformate (13.66 g; 0.1 mol) and 50 ml of a 2N solution of sodium hydroxide are added simultaneously. After stirring for 16 hours at 23° C., approximately 10 ml of a solution of concentrated hydrochloric acid (approximately 11 N) is added in order to adjust the pH to 4-5. The oil obtained is extracted with ethyl acetate (2×50 ml), washed with water then dried over magnesium sulphate. The product crystallizes from isopentane in the form of a white powder (yield of 68%). Melting point: 50.5° C.

Workup

  1. additionare added simultaneously
  2. customThe oil obtained
  3. extractionis extracted with ethyl acetate (2×50 ml)
  4. washwashed with water
  5. dry with materialthen dried over magnesium sulphate

Sources & evidence

ORD record
ord-0662cf9f703d4679b430dda585fd6e11
Source dataset
uspto-grants-2007_11
Patent number
US07291641B2

Reaction notes

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