HCID 53860091, compound → HCID 13037304, compound

HRID 1085432Notes

Reaction equation

HRID 1085432 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-d14fd78c64b546149d99b208022716fd
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

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