2,4,5-Trichlorophenol → HCID 15159979, compound

HRID 256332Notes

Reaction equation

HRID 256332 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:23][CH3:24])[C@@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(Cl)C(Cl)=CC=1O.C1(N=C=NC2CCCCC2)CCCCC1.[NH:50]1[CH2:57][CH2:56][CH2:55][C@H:51]1[C:52]([OH:54])=[O:53].C(N(CC)CC)C>O1CCCC1.C1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]([CH2:23][CH3:24])[C@@H:12]([C:20]([N:50]1[CH2:57][CH2:56][CH2:55][C@H:51]1[C:52]([OH:54])=[O:53])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 72712,4,5-TrichlorophenolHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 145742L-Proline2×HCID 13146030HCID 13146030, compound

Product 1

HCID 15159979HCID 15159979, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.6 g (0.008 mole) of N-benzyloxycarbonyl-N-ethyl-D-phenylalanine (Example 3, Step 2) are dissolved in 10 ml of tetrahydrofuran and at 0° C. 1.6 g (0.008 mole) of 2,4,5-trichlorophenol and 1.65 g (0.008 mole) of dicyclohexylcarbodiimide are added, then the mixture is left to stand at room temperature for 4 hours. The residue is dissolved in 40 ml of benzene, washed twice with 20 ml of a 5 percent solution of sodium hydrogen carbonate, twice with 20 ml of water, then it is dried over anhydrous sodium sulfate and evaporated on a water bath having a temperature of about 40° C. at 15 to 20 millibars. The residual oil is dissolved in 10 ml of pyridine, 0.92 g (0.008 mole) of L-proline and 1.12 ml (0.008 mole) of triethylamine are added and the mixture is stirred till the dissolution of proline at room temperature. Then the solution is left to stand for 4 to 5 hours, subsequently it is evaporated on a water bath having a temperature of about 40° C. at 15 to 20 millibars. The residue is dissolved in a mixture of 25 ml of water and 10 ml of diethyl ether. The aqueous layer is washed twice with 10 ml of diethyl ether and the combined ether extracts are washed with 10 ml of a 5 percent solution of sodium hydrogen carbonate. The aqueous layers are combined and acidified to pH 2 with 3N hydrochloric acid. The separated product is extracted three times with 15 ml of benzene, the benzene layers are combined, washed three times with 5 ml of water, dried over anhydrous sodium sulfate and evaporated on a water bath having a temperature of about 40° C. at 15 to 20 millibars. Yield 2.2 g (64%) of an oil.

Workup

  1. waitthe mixture is left
  2. washwashed twice with 20 ml of a 5 percent solution of sodium hydrogen carbonate, twice with 20 ml of water
  3. dry with materialit is dried over anhydrous sodium sulfate
  4. customevaporated on a water bath
  5. customa temperature of about 40° C.
  6. dissolutionThe residual oil is dissolved in 10 ml of pyridine
  7. waitThen the solution is left
  8. waitto stand for 4 to 5 hours
  9. customsubsequently it is evaporated on a water bath
  10. customa temperature of about 40° C.
  11. dissolutionThe residue is dissolved in a mixture of 25 ml of water and 10 ml of diethyl ether
  12. washThe aqueous layer is washed twice with 10 ml of diethyl ether
  13. washthe combined ether extracts are washed with 10 ml of a 5 percent solution of sodium hydrogen carbonate
  14. extractionThe separated product is extracted three times with 15 ml of benzene
  15. washwashed three times with 5 ml of water
  16. dry with materialdried over anhydrous sodium sulfate
  17. customevaporated on a water bath
  18. customa temperature of about 40° C.

Sources & evidence

ORD record
ord-d1157e4dd45c4f63ae77381bb2c1d47d
Source dataset
uspto-grants-1987_10
Patent number
US04703036

Reaction notes

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