Réaction #414690

ord-0077a8c84fcd4387a03e58edec17eae8

Équation de réaction

Cc1ccc(S(=O)(=O)O)cc1.NCCC(=O)OCc1ccccc1
β-alanine benzyl ester p-toluenesulphonate
CC(C)(C)OC(=O)N1CCCC(C(=O)O)C1
rac-N-(t-butoxycarbonyl)piperidine-3-carboxylic acid
COc1nnnc(OC)c1Cl
chlorodimethoxytriazine
CN1CCOCC1
N-methylmorpholine
CN1CCOCC1
N-methyl-morpholine
→
CC(C)(C)OC(=O)N1CCCC(C(=O)NCCC(=O)OCc2ccccc2)C1
rac-N-[[1-(t-butoxycarbonyl)-3-piperidinyl]-carbonyl]-β-alanine benzyl ester

Réactifs

Cc1ccc(S(=O)(=O)O)cc1.NCCC(=O)OCc1ccccc1
β-alanine benzyl ester p-toluenesulphonate
CC(C)(C)OC(=O)N1CCCC(C(=O)O)C1
rac-N-(t-butoxycarbonyl)piperidine-3-carboxylic acid
COc1nnnc(OC)c1Cl
chlorodimethoxytriazine
CN1CCOCC1
N-methylmorpholine
CN1CCOCC1
N-methyl-morpholine

Réactifs

Aucun

Solvants

C1CCOC1
THF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

rac-N-(t-butoxycarbonyl)piperidine-3-carboxylic acid (Can. J. Physiol. Pharmacol. 57, 1979, 763) in THF was activated with chlorodimethoxytriazine and N-methyl-morpholine and then coupled with β-alanine benzyl ester p-toluenesulphonate (J. Org. Chem. 17, 1952, 1564) and N-methylmorpholine to give rac-N-[[1-(t-butoxycarbonyl)-3-piperidinyl]-carbonyl]-β-alanine benzyl ester, m.p. 57°-59° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05273982uspto-grants-1993_12