Premium
Reaction of 5‐hydroxy‐L‐tryptophan with alkyl isocyanates
Author(s) -
Braña Miguel F.,
Garrido Mercedes,
Hernando José L.,
Rodríguez María L. LÓPez,
Morcillo M. José
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240643
Subject(s) - chemistry , acetone , isopropyl , tryptophan , alkyl , hydantoin , cyanate , organic chemistry , potassium carbonate , medicinal chemistry , amino acid , biochemistry
5‐Hydroxy‐L‐tryptophan 4 with potassium cyanate gives 5‐(5‐hydroxy‐3‐indolylmethyl)hydantoin 5 or N b ‐carbamoyl‐5‐hydroxy‐L‐tryptophan 6 depending on the reaction conditions. Reaction of 4 with methyl iso‐cyanate in acetone provides 5‐hydroxy‐ N b ‐methylcarbamoyl‐L‐tryptophan 7 . Treatment of 4 with ethyl, propyl and isopropyl isocyanates in acetone gives rise to the formation of the corresponding 2‐[(3‐alkyl‐4,4‐dimethyl‐2‐oxo)‐1,3‐diazetidinyl]‐3‐(5‐hydroxy‐3‐indolyl)propionic acids 8–10 .
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom