Triethylamine → HCID 53782825, compound

HRID 1390273Notes

Reaction equation

HRID 1390273 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[C:22](=[S:24])=O.[CH3:25][C:26]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][C:27]=1[CH2:28]Cl>C(Cl)(Cl)Cl>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:22]([CH2:28][C:27]1[CH:30]=[C:31]([CH3:34])[CH:32]=[CH:33][C:26]=1[CH3:25])=[S:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10039Carbonyl SulfideHCID 69987Benzene, 2-(chloromethyl)-1,4-dimethyl-HCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 53782825HCID 53782825, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

10.8 G (0.05 mol) of L-phenylalanine methylester hydrochloride was added to 100 ml of chloroform. To the mixture was added 13.9 ml (0.1 mol) of triethylamine while cooling with ice. 20 Ml of a chloroform solution containing 3.0 g (0.05 mol) of carbonyl sulfide was dropwise added to the solution at a temperature of from 5° to 10° C. in 20 minutes. After stirring at the same temperature for 30 minutes, 30 ml of chloroform solution containing 7.7 g (0.05 mol) of 2.5-dimethylbenzylchloride was dropwise added to the solution in 30 minutes. After this, the mixture was stirred at room temperature for 1 hour. After completion of reaction, the reaction mixture was washed with 100 ml of water, 100 ml of 2N-hydrochloric acid and 150 ml of water in order twice and was dried over anhydrous sodium sulfate in a similar manner to that described in Example 2. After filtration of the drying agent, the syrup-like substance obtained by removing the solvent of the filtrate in vacuo was crystallized from 30 ml of ethylacetate and 50 ml of n-hexane to yield 10.8 g of white crystals.

Workup

  1. temperaturewhile cooling with ice
  2. additionwas dropwise added to the solution at a temperature of from 5° to 10° C. in 20 minutes
  3. additionwas dropwise added to the solution in 30 minutes
  4. stirringAfter this, the mixture was stirred at room temperature for 1 hour
  5. customAfter completion of reaction
  6. washthe reaction mixture was washed with 100 ml of water, 100 ml of 2N-hydrochloric acid and 150 ml of water in order twice
  7. dry with materialwas dried over anhydrous sodium sulfate in a similar manner to that
  8. filtrationAfter filtration of the drying agent
  9. customthe syrup-like substance obtained
  10. customby removing the solvent of the filtrate in vacuo
  11. customwas crystallized from 30 ml of ethylacetate and 50 ml of n-hexane

Sources & evidence

ORD record
ord-5570132dd6dd440597a724f878130808
Source dataset
uspto-grants-1979_02
Patent number
US04138485

Reaction notes

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