Pentachlorophenol → HCID 57205679, compound

HRID 867077Notes

Reaction equation

HRID 867077 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[C:27](O)=[C:26]([Cl:29])[C:25]([Cl:30])=[C:24]([Cl:31])[C:23]=1[Cl:32].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[Cl:21][C:22]1[C:27]([O:19][C:18](=[O:20])[CH2:17][NH:16][C:14](=[O:15])[C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[C:26]([Cl:29])[C:25]([Cl:30])=[C:24]([Cl:31])[C:23]=1[Cl:32]

Participants

5

Reactant 3

HCID 992PentachlorophenolHCID 10868DicyclohexylcarbodiimideHCID 7016875HCID 7016875, compound

Product 1

HCID 57205679HCID 57205679, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

1.9 g. (6.2 mmole) of tert.-butyloxycarbonyl-L-methionyl-glycine [M.A. Ondetti, I. Phuscec, E.F. Sabo, J.T. Sheehan, N-Williams; J. Am. Chem. Soc. 92, 195 (1970)] and 1.92 g. (7.2 mmole) of pentachlorophenol are dissolved in 31 ml. of dimethyl formamide. The solution is cooled to 0° C., the solution of 1.41 g. (6.85 mmole) of dicyclohexyl carbodiimide in 6.2 ml. of dimethyl formamide is added dropwise under stirring and the mixture is stirred for a further hour at the same temperature. The mixture is allowed to stand over night; on the following day the precipitated dicyclohexyl urea is filtered off and the filtrate is evaporated to dryness under reduced pressure. The evaporation residue is triturated with ether, the product filtered, washed with a minor amount of ether and recrystallized from a 15-fold amount of ether. 2.19 g. of tert.-butyloxycarbonyl-L-methionyl-glycine pentachlorophenyl ester (63.6% of the theoretical yield) are obtained; m.p. 169°-171° C.; Rf (in the 8:2 mixture of chloroform and ethanol) = 0.8.

Workup

  1. stirringthe mixture is stirred for a further hour at the same temperature
  2. waitto stand over night
  3. filtrationon the following day the precipitated dicyclohexyl urea is filtered off
  4. customthe filtrate is evaporated to dryness under reduced pressure
  5. customThe evaporation residue is triturated with ether
  6. filtrationthe product filtered
  7. washwashed with a minor amount of ether
  8. customrecrystallized from a 15-fold amount of ether

Sources & evidence

ORD record
ord-d03e6dc70f404209a2137c84007f3aa0
Source dataset
uspto-grants-1978_07
Patent number
US04102878

Reaction notes

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