2,4,5-Trichlorophenol → N-(1,1-dimethylethoxycarbonyl)leucine 2,4,5-trichlorophenyl ester

HRID 53085Notes

Reaction equation

HRID 53085 reaction equation
[CH3:1][C:2]([CH3:16])([O:4][C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH3:3].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1O.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1[O:14][C:13](=[O:15])[C@H:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH:7][C:5]([O:4][C:2]([CH3:3])([CH3:1])[CH3:16])=[O:6]

Participants

5

Reactant 3

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 15431614N-(1,1-dimethylethoxycarbonyl)leucine 2,4,5-trichlorophenyl esterYield 100.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(1,1-Dimethylethoxycarbonyl)leucine (6.32 g, 15 mmol) was stirred with 2,4,5-trichlorophenol (3.01 g, 15.2 mmol) and dicyclohexylcarbodiimide (3.14 g, 15.2 mmol) in ethyl acetate (50 mL) at -10° 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)leucine 2,4,5-trichlorophenyl ester (6.2 g, 99%).

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-03579b5b559c4d1b83d5f3479325a6db
Source dataset
uspto-grants-1997_04
Patent number
US05618528

Reaction notes

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