Diethyl Ether → HCID 53703293, compound

HRID 1390275Notes

Reaction equation

HRID 1390275 reaction equation
Br.[CH3:2][O:3][C:4](=[O:25])[C@H:5]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9].CCOCC.[CH3:31][C:32]1[CH:41]=[CH:40][C:35]([CH2:36][C:37](Cl)=[S:38])=[CH:34][CH:33]=1.C(N(CC)CC)C>O>[CH3:2][O:3][C:4](=[O:25])[C@H:5]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[NH:9][C:37]([CH2:36][C:35]1[CH:40]=[CH:41][C:32]([CH3:31])=[CH:33][CH:34]=1)=[S:38]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 22806806HCID 22806806, compoundHCID 53701717HCID 53701717, compound

Product 1

HCID 53703293HCID 53703293, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.0 G (0.01 mol) of L-phenylalanyl-L-phenylalanine methylester hydrobromide was dissolved in 50 ml of water. To the solution was added 10 ml of an ether solution containing 2.21 g (0.011 mol) of 4-methylbenzylthiocarbonylchloride and was further dropwise added an aqueous solution containing 2.28 g (0.022 mol) of triethylamine for 15 minutes. After this, the mixture was stirred for 30 minutes while cooling with ice and was further stirred at room temperature for 4 hours. After completion of reaction, the reaction mixture was extracted with about 50 ml of ethylacetate. The ethylacetate layer was washed with 2N hydrochloric acid and then with water and was dried over anhydrous sodium sulfate. After drying, the drying agent was filtered. After removing the solvent of filtrate by evaporation in vacuo, the resultant solid material was recrystallized from 25 ml of ethylacetate and about 40 ml of n-hexane to obtain 3.7 g of white crystals.

Workup

  1. additionwas further dropwise added an aqueous solution
  2. temperaturewhile cooling with ice
  3. stirringwas further stirred at room temperature for 4 hours
  4. customAfter completion of reaction
  5. extractionthe reaction mixture was extracted with about 50 ml of ethylacetate
  6. washThe ethylacetate layer was washed with 2N hydrochloric acid
  7. dry with materialwith water and was dried over anhydrous sodium sulfate
  8. customAfter drying
  9. filtrationthe drying agent was filtered
  10. customAfter removing the solvent of filtrate
  11. customby evaporation in vacuo
  12. customthe resultant solid material was recrystallized from 25 ml of ethylacetate and about 40 ml of n-hexane

Sources & evidence

ORD record
ord-1405eba1400646a49f02abe28dca8532
Source dataset
uspto-grants-1979_02
Patent number
US04138485

Reaction notes

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