L-Phenylalanine → HCID 54152741, compound

HRID 1390270Notes

Reaction equation

HRID 1390270 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.O1CCOCC1.[C:26](=[S:28])=O.[CH3:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1>O>[CH3:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][C:26]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[S:28])=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 6140L-PhenylalanineHCID 77224-Methylbenzyl chlorideHCID 8471TriethylamineHCID 10039Carbonyl SulfideHCID 312751,4-Dioxane

Product 1

HCID 54152741HCID 54152741, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

16.5 G (0.1 mol) of L-phenylalanine and 27.8 ml (0.2 mol) of triethylamine were dissolved in 100 ml of water. To this solution was added dropwise 150 ml of dioxane containing 6.0 g (0.1 mol) of carbonyl sulfide at a temperature of from 5°to 10° C in 15 minutes while cooling with ice. After stirring at a temperature of 10° C for 15 minutes, 14.1 g (0.1 mol) of 4-methylbenzylchloride was added dropwise to the solution in 10 minutes and the solution was then stirred at room temperature for 1 hour. After completion of the reaction, a syrup-like substance was formed in a similar manner to that described in Example 1, which was then crystallized from 60 ml of ethylacetate and 300 ml of petroleum ether to obtain 25.7 g of white crystals.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe solution was then stirred at room temperature for 1 hour
  3. customAfter completion of the reaction
  4. customa syrup-like substance was formed in a similar manner to that
  5. customwas then crystallized from 60 ml of ethylacetate and 300 ml of petroleum ether

Sources & evidence

ORD record
ord-73d1522a07ae417ea6e6b6d6f63b8a4c
Source dataset
uspto-grants-1979_02
Patent number
US04138485

Reaction notes

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