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

HRID 1459142Notes

Reaction equation

HRID 1459142 reaction equation
[CH3:1][C:2]([CH3:12])([O:4][C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6])[CH3:3].[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:10][C:9](=[O:11])[CH2:8][NH:7][C:5]([O:4][C:2]([CH3:12])([CH3:1])[CH3:3])=[O:6]

Participants

5

Reactant 3

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

Product 1

HCID 12799284t-Butoxycarbonylglycine-2,4,5-Trichlorophenyl EsterYield 99.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(1,1-Dimethylethoxycarbonyl)glycine (6.12 9, 35 mmol) was stirred with 2,4,5-trichlorophenol (6.91 g, 35 mmol) and dicyclohexylcarbodiimide (7.22 g, 35 mmol) in ethyl acetate (100 mL) at 0° C. for 4 h. The suspension was filtered and the solvent was evaporated under reduced pressure from the filtrate. The residue was dissolved in ethyl acetate. The suspension was filtered and the solvent was evaporated under reduced pressure from the filtrate to give N-(1,1-dimethylethoxycarbonyl)glycine 2,4,5-trichlorophenyl ester (12.4 g, quantitative).

Workup

  1. filtrationThe suspension was filtered
  2. customthe solvent was evaporated under reduced pressure from the filtrate
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationThe suspension was filtered
  5. customthe solvent was evaporated under reduced pressure from the filtrate

Sources & evidence

ORD record
ord-c729a95712f24385a435283a64c6d236
Source dataset
uspto-grants-1998_12
Patent number
US05853713

Reaction notes

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