Ammonia → benzyl N-(2-carbamoylethyl)carbamate

HRID 1833327Notes

Reaction equation

HRID 1833327 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19](CC)CC)C.C(OC(Cl)=O)C(C)C.N>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH2:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 75313N-Benzyloxycarbonyl-beta-alanine

Product 1

HCID 324693benzyl N-(2-carbamoylethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

111.7 g of benzyloxycarbonyl-β-alanine were dissolved in 1 liter of dimethylformamide, cooled to -20° C, treated with 70 ml of triethylamine and 67 ml of chloroformic acid isobutyl ester and stirred at -20° C for 3 minutes. Dry ammonia gas was led into this mixture until the pH rose to 11, care being taken that the temperature did not, exceed -10° C. The mixture was stirred for a further 30 minutes at room temperature, filtered and the filtrate concentrated in vacuo. The residue was recrystallised from water. Yield: 91 g; melting point 162°-165° C.

Workup

  1. customexceed -10° C
  2. stirringThe mixture was stirred for a further 30 minutes at room temperature
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was recrystallised from water

Sources & evidence

ORD record
ord-b937ca86ce254ef1a0c438fd8ef55554
Source dataset
uspto-grants-1978_01
Patent number
US04066635

Reaction notes

Loading…