(1R,2S)-Tranylcypromine → HCID 58842375, compound

HRID 1270443Notes

Reaction equation

HRID 1270443 reaction equation
[CH2:1]1[C@@H:3]([NH2:4])[C@@H:2]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:11]([CH:14]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([O:17]CC)=O)=[C:12]=[O:13]>ClCCl>[CH2:20]([CH:14]1[NH:11][C:12](=[O:13])[N:4]([CH2:3][C:2]2([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:1][CH2:5][CH2:2][CH2:1][CH2:3]2)[C:15]1=[O:17])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 19493(1R,2S)-TranylcypromineHCID 12370705Ethyl N-(oxomethylidene)phenylalaninate

Product 1

HCID 58842375HCID 58842375, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 1 (0.255 g; 1.35 mmol) in anhydrous dichloromethane (8 mL) was treated with ethyl 2-isocyanato-3-phenylpropionate (0.325 g; 0.38 mmol) and stirred at room temperature overnight. The solvent was removed by evaporation, the residue was dissolved in ethanol (1 mL), 6N hydrochloric acid (0.5 mL) and water (0.5 mL) and the reaction mixture was heated to 50° C. After 3 h at 50° C., additional 6N hydrochloric acid (1 mL) was added and the reaction mixture was heated at 65° C. overnight. The reaction mixture was concentrated and the crude product was purified directly by column chromatography on silica gel using 1:1 ethyl acetate:hexane as the eluent to give 0.053 g of 5-Benzyl-3-(1-phenyl-cyclohexylmethyl)-imidazolidine-2,4-dione as a white solid. Mass Spec [M+H]+=363.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in ethanol (1 mL)
  3. temperature6N hydrochloric acid (0.5 mL) and water (0.5 mL) and the reaction mixture was heated to 50° C
  4. waitAfter 3 h at 50° C.
  5. additionadditional 6N hydrochloric acid (1 mL) was added
  6. temperaturethe reaction mixture was heated at 65° C. overnight
  7. concentrationThe reaction mixture was concentrated
  8. customthe crude product was purified directly by column chromatography on silica gel using 1:1 ethyl acetate

Sources & evidence

ORD record
ord-8ca88ec8d5c94c61bb35106fd54c435b
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

Loading…