2,4,5-Trichlorophenol → t-Butoxycarbonylglycine-2,4,5-Trichlorophenyl Ester

HRID 1863465Notes

Reaction equation

HRID 1863465 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[CH:16][C:15]=1O.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[CH:16][C:15]=1[O:11][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

5

Reactant 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 12799284t-Butoxycarbonylglycine-2,4,5-Trichlorophenyl Ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepare and chill a solution of 14 g. of t-butoxycarbonylglycine and 15.8 g. of 2,4,5-trichlorophenol in 200 ml. of ethyl acetate. Add with stirring 18.2 g. of dicyclohexylcarbodiimide in small portions. Stir the reaction mixture at room temperature for 16 hours, filter and evaporate the filtrate to a residue. Wash the residue by triturating with hexane, then crystallize from ethyl ether to obtain thereby the title product (m.p. 100°-103° C.).

Workup

  1. customPrepare
  2. temperaturechill a solution of 14 g
  3. additionAdd
  4. stirringStir the reaction mixture at room temperature for 16 hours
  5. filtrationfilter
  6. customevaporate the filtrate to a residue
  7. washWash the residue
  8. customby triturating with hexane
  9. customcrystallize from ethyl ether
  10. customto obtain

Sources & evidence

ORD record
ord-5828a17828fa4e05891526cd21798a17
Source dataset
uspto-grants-1979_09
Patent number
US04169141

Reaction notes

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