Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Carbonyl Sulfide | HCID 10039 | — |
| Reactant | Benzene, 2-(chloromethyl)-1,4-dimethyl- | HCID 69987 | — |
| Reactant | Methyl L-phenylalaninate hydrochloride | HCID 75736 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | HCID 53782825 | HCID 53782825 | 63.3% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04138485 |
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| Source dataset | uspto-grants-1979_02 |
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| ORD ID | ord-5570132dd6dd440597a724f878130808 |
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| Source note | uspto-grants-1979_02 |
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