HCID 53860091, compound → HCID 13037304, compound

HRID 1757962Notes

Reaction equation

HRID 1757962 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C@H:5]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:19]#[N:20])[NH:12][CH:11]=1)[NH:6][CH:7]=O)[CH3:2]>P(Cl)(Cl)(Cl)=O>[CH2:1]([O:3][C:4]([CH:5]1[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[C:19]#[N:20])[NH:12][C:11]=2[CH2:7][NH:6]1)=[O:21])[CH3:2]

Participants

3

Reactant 1

HCID 53860091HCID 53860091, compound

Product 1

HCID 13037304HCID 13037304, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

7.8 g of 4-cyano-N-formyltryptophan ethyl ester is dissolved at 0° C. in 40 ml of phosphorus oxychloride and stirred for 18 hours at room temperature. The solution is then concentrated by evaporation in vacuo, the residue partitioned between water and chloroform and the aqueous phase then extracted. The organic phases are washed with water, dried with calcium sulphate and concentrated by evaporation in vacuo. Chromatography on silica gel with methylene chloride-acetone (1:1) of the residue yields 300 mg of 5-cyano-1,2,3,4-tetrahydro-β-carbolin-3-carboxylic acid ethyl ester of melting point 248° C. in addition to 500 mg of 5-cyano-β-carbolin-3-carboxylic acid ethyl ester of melting point 310° C., by disproportionation of the 5-cyano-3,4-dihydro-β-carbolin-3-carboxylic acid ethyl ester.

Workup

  1. concentrationThe solution is then concentrated by evaporation in vacuo
  2. customthe residue partitioned between water and chloroform
  3. extractionthe aqueous phase then extracted
  4. washThe organic phases are washed with water
  5. dry with materialdried with calcium sulphate
  6. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-f5af441bf8da44a0b0d0d8d32f5e0d48
Source dataset
uspto-grants-1983_02
Patent number
US04371536

Reaction notes

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