Crystallization-induced diastereoselection: asymmetric synthesis of substance P inhibitors.
A novel three-component condensation followed by a crystallization-induced asymmetric transformation is used to build this key substance P inhibitor intermediate in a short synthetic sequence.
Pye
Philip J
PJ
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. philip_pye@merck.com
Rossen
Kai
K
Weissman
Steven A
SA
Maliakal
Ashok
A
Reamer
Robert A
RA
Ball
Richard
R
Tsou
Nancy N
NN
Volante
R P
RP
Reider
Paul J
PJ
D000818:Animals; D000928:Antidepressive Agents / Q000138:chemical synthesis*; D003460:Crystallization; D006801:Humans; D006900:Hydroxylation; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013373:Substance P / Q000037:antagonists & inhibitors*; D014230:Triazoles / Q000138:chemical synthesis*
C473334:2-(4-fluorophenyl)-1-(3-oxo-(2H,4H)-1,2,4-triazol-5-ylmethyl)-3-(1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)morpholine; D000928:Antidepressive Agents; D009025:Morpholines; D014230:Triazoles; D013373:Substance P