2,4,5-Trichlorophenol → HCID 70100887, compound

HRID 1977587Notes

Reaction equation

HRID 1977587 reaction equation
C1([NH2+]C2CCCCC2)CCCCC1.[CH3:14][O:15][C:16]([NH:18][C@@H:19]([C:27]([O-:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17].OS([O-])(=O)=O.[K+].[Cl:36][C:37]1[CH:42]=[C:41]([Cl:43])[C:40]([Cl:44])=[CH:39][C:38]=1O.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[Cl:36][C:37]1[CH:42]=[C:41]([Cl:43])[C:40]([Cl:44])=[CH:39][C:38]=1[O:28][C:27](=[O:29])[C@@H:19]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:18][C:16]([O:15][CH3:14])=[O:17]

Participants

6

Reactant 4

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 516920Potassium bisulfateHCID 141589101HCID 141589101, compound

Product 1

HCID 70100887HCID 70100887, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

11.3 g (28 mmol) of methoxycarbonyl-3-phenyl-D-alanine dicyclohexylammonium salt (Synthesis 2, Step A) is distributed between 75 ml of ethyl acetate and 30.5 ml of 1M KHSO4. The phases are separated, the organic phase is washed neutral with water, dried over anhydrous sodium sulphate and concentrated at a pressure of 2.0-2.5 kPa to a volume of 15 ml. To the cooled (approx. 0° C.) residue 5.5 g (28 mmol) of 2,4,5-trichlorophenol and 5,75 g (28 mmol) of dicyclohexyl carbodiimide are added and the reaction mixture is allowed to stand overnight. The separated dicyclohexylurea is filtered off, and the filtrate evaporated. The oily residue is crystallised from ethanol. The crystals are filtered, washed with diethyl ether and dried in a vacuum desiccator.

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed neutral with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated at a pressure of 2.0-2.5 kPa to a volume of 15 ml
  5. additionare added
  6. filtrationThe separated dicyclohexylurea is filtered off
  7. customthe filtrate evaporated
  8. customThe oily residue is crystallised from ethanol
  9. filtrationThe crystals are filtered
  10. washwashed with diethyl ether
  11. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-1d82a727772b483689764560f37704ec
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

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