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

HRID 53087Notes

Reaction equation

HRID 53087 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 g, 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-7ab8d17c269e40cca2abf743da08dda4
Source dataset
uspto-grants-1997_04
Patent number
US05618528

Reaction notes

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