L-Tryptophan → Perylene

HRID 2176473Notes

Reaction equation

HRID 2176473 reaction equation
N[C@H:2]([C:13](O)=O)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)N[CH:5]=1.CN1[C:21](=O)[CH2:20][CH2:19][CH2:18]1>O>[CH:3]1[C:4]2=[C:12]3[C:7]([C:18]4[C:13]5[C:2](=[CH:3][CH:4]=[CH:5][C:5]2=5)[CH:21]=[CH:20][CH:19]=4)=[CH:8][CH:9]=[CH:10][C:11]3=[CH:13][CH:2]=1

Participants

4

Reactant 2

HCID 6305L-Tryptophan2×HCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 9142Perylene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.15 mg Trp were dissolved in a minimal amount of water by addition of a molar amount of NaCO3 and sonication. The Trp solution was added to the PDI-NMP-NHS solution and was stirred over night. The compound was transferred to a separating funnel and the aqueous phase was washed with DCM. Then the aqueous phase was acidified to pH 2 using 0.1 M HCl and extracted to DCM. The organic phase was washed 3 times with KCl brine. The extract was concentrated and precipitated from hexane and from diethyl-ether, the precipitant was filtered and re-dissolved in DCM. NMR and mass were measured.

Workup

  1. customThe compound was transferred to a separating funnel
  2. washthe aqueous phase was washed with DCM
  3. extractionextracted to DCM
  4. washThe organic phase was washed 3 times with KCl brine
  5. concentrationThe extract was concentrated
  6. customprecipitated from hexane and from diethyl-ether
  7. filtrationthe precipitant was filtered
  8. dissolutionre-dissolved in DCM

Sources & evidence

ORD record
ord-7ba5a12ea1d0465da8da015faaa86e39
Source dataset
uspto-grants-2015_06
Patent number
US09067181B2

Reaction notes

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