L-Phenylalanine → HCID 22806795, compound

HRID 1390272Notes

Reaction equation

HRID 1390272 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.[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1)([O-:22])=[O:21].[C:31](=[S:33])=O>O.O1CCOCC1>[N+:20]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27][C:31]([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:33])=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 6140L-PhenylalanineHCID 74824-Nitrobenzyl chlorideHCID 8471TriethylamineHCID 10039Carbonyl Sulfide

Product 1

HCID 22806795HCID 22806795, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

8.3 G (0.05 mol) of L-phenylalanine and 13.9 ml (0.1 mol) of triethylamine were dissolved in 50 ml of water. To the solution was added 100 ml of dioxane solution containing 8.6 g (0.5 mol) of 4-nitrobenzylchloride. 3.0 g (0.05 mol) of carbonyl sulfide was blown into the solution at a temperature of from 10° to 15° C. in 15 minutes. After completion of blowing, the mixture was subjected to reaction at room temperature for 2 hours. After completion of reaction, the solid material obtained in a similar manner to that described in Example 1 was recrystallized from 50 ml of ethylacetate and 20 ml of n-hexane to yield 9.4 g of pale yellow crystals.

Workup

  1. customthe mixture was subjected to reaction at room temperature for 2 hours
  2. customAfter completion of reaction
  3. customthe solid material obtained in a similar manner to that
  4. customwas recrystallized from 50 ml of ethylacetate and 20 ml of n-hexane

Sources & evidence

ORD record
ord-17d2d6b154e94dfc86228b9293a7fca7
Source dataset
uspto-grants-1979_02
Patent number
US04138485

Reaction notes

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