Hydrochloric Acid → Phenylacetic Acid

1.34 g of 7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazole-5-carboxylic acid was suspended in 20 ml of methylene chloride and 0.85 ml of triethylamine was added to the suspension while ice-cooling followed by allowing the mixture to react for 10 minutes. Then, 0.85 ml of isobutyl chloroformate was added thereto dropwise and allowed to react for 30 minutes at the same temperature as above. To the reaction mixture were added 110 ml of a 10% aqueous sodium hydroxide solution having dissolved therein 0.9 g of D-(-)-phenylglycine at the same temperature as above and then 80 ml of dimethylformamide followed by allowing the mixture to react for 3 hours. After completion of the reaction, the reaction mixture was rendered neutral with a 6 N hydrochloric acid and the solvent was removed under reduced pressure. 20 ml of water and 100 ml of a 10% aqueous sodium hydroxide solution were added to the residue to dissolve it and the solution was treated with activated carbon and filtered. The filtrate was adjusted to a pH of 2 with concentrated hydrochloric acid to obtain light yellow crystals, which were washed with water, dried, mixed with 50 ml of chloroform with stirring and filtered. The filtrate was mixed with 30 ml of petroleum ether to obtain 1.1 g of D-(-)-2-7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazole-5-carboxamido)phenylacetic acid as light yellow needles having a melting point of 165° to 167° C.

1. temperaturecooling
2. customto react for 10 minutes
3. customto react for 30 minutes at the same temperature as above
4. dissolutionhaving dissolved
5. customto react for 3 hours
6. customAfter completion of the reaction
7. customthe solvent was removed under reduced pressure
8. addition20 ml of water and 100 ml of a 10% aqueous sodium hydroxide solution were added to the residue
9. dissolutionto dissolve it
10. additionthe solution was treated with activated carbon
11. filtrationfiltered
12. customto obtain light yellow crystals, which
13. washwere washed with water
14. customdried
15. additionmixed with 50 ml of chloroform
16. filtrationfiltered
17. additionThe filtrate was mixed with 30 ml of petroleum ether

ORD record

ord-d2db3ef5e5094dcaae35084ad3e51a8e

Source dataset

uspto-grants-1982_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04317820