Pentachlorophenol → N-t-butoxycarbonyl-leucyl-glycine-pentachlorophenyl ester

HRID 1248744Notes

Reaction equation

HRID 1248744 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][CH:11]([CH3:13])[CH3:12])=[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>O1CCCC1>[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][CH:11]([CH3:12])[CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[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 7018768(S)-2-(2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)acetic acid

Product 1

HCID 18598487N-t-butoxycarbonyl-leucyl-glycine-pentachlorophenyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 300 ml of tetrahydrofuran were dissolved 40.0 g of N-t-butoxycarbonyl-leucyl-glycine and 38.8 g of pentachlorophenol, after which 30.0 g of dicyclohexylcarbodiimide (DCC) was added with ice-cooling, and the resulting mixture was subjected to reaction overnight. The insoluble material was collected by filtration and the solvent was removed by distillation to obtain a solid, which was recrystallized from ethyl acetate and petroleum ether to obtain N-t-butoxycarbonyl-leucyl-glycine-pentachlorophenyl ester. Yield: 65.9 g (88.5%). [α]D24 =-23.4° (C=1, dimethylformamide). Melting point (Mp): 155°-157° C.

Workup

  1. temperaturecooling
  2. customthe resulting mixture was subjected to reaction overnight
  3. filtrationThe insoluble material was collected by filtration
  4. customthe solvent was removed by distillation
  5. customto obtain a solid, which
  6. customwas recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-aa12b83506844d798a7fe4b5d3b867a8
Source dataset
uspto-grants-1985_06
Patent number
US04525576

Reaction notes

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