Réaction #351875

ord-5e1928c7e88b4cb4ad2152527840d964

Équation de réaction

N[C@H]1CCN(C(=O)c2cc(Cl)cc(Cl)c2)[C@H](Cc2ccccc2)C1
(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine
O=C(O)c1c[nH]c2ccccc12
indole-3-carboxylic acid
O=C1OCCN1P(=O)(Cl)N1CCOC1=O
bis(2-oxo-3-oxazolidinyl)phosphinic chloride
CCN(CC)CC
triethylamine
→
O=C(N[C@H]1CCN(C(=O)c2cc(Cl)cc(Cl)c2)[C@H](Cc2ccccc2)C1)c1c[nH]c2ccccc12
title compound
O=C(N[C@H]1CCN(C(=O)c2cc(Cl)cc(Cl)c2)[C@H](Cc2ccccc2)C1)c1c[nH]c2ccccc12
(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-N-(3-indolylcarbonyl)-4-piperidinamine

Réactifs

N[C@H]1CCN(C(=O)c2cc(Cl)cc(Cl)c2)[C@H](Cc2ccccc2)C1
(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine
O=C(O)c1c[nH]c2ccccc12
indole-3-carboxylic acid
O=C1OCCN1P(=O)(Cl)N1CCOC1=O
bis(2-oxo-3-oxazolidinyl)phosphinic chloride
CCN(CC)CC
triethylamine

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

200 mg (0.550 mmol) of (2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine are reacted in analogy to Example 4a with 106 mg (0.661 mmol) of indole-3-carboxylic acid, 168 mg (0.661 mmol) of bis(2-oxo-3-oxazolidinyl)phosphinic chloride and 169 μl (1.21 mmol) of triethylamine. The title compound ##STR86## is obtained (92 mg, 33%) as oil. TLC:methylene chloride/methanol/cone. ammonia (350:50:1) Rf =0.61, FD-MS:M+ =505, 507; IR:3450, 3260, 1770, 1635 cm-1.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05646144uspto-grants-1997_07