Реакция #172832

ord-de6033d180274902adc024db54ab88e3

Уравнение реакции

C=C(C)[C@@H]1CC[C@]2(NCC(=O)N(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(c6ccc(C(=O)O)cc6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)-2-oxoethylamino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid
Cl.ClCCN1CCOCC1
4-(2-chloroethyl)morpholine hydrochloride
C=C(C)[C@@H]1CC[C@]2(NCCN3CCOCC3)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(c6ccc(C(=O)O)cc6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
title compound
C=C(C)[C@@H]1CC[C@]2(NCCN3CCOCC3)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(c6ccc(C(=O)O)cc6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(2-morpholinoethylamino)-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

The title compound was prepared following the method described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)-2-oxoethylamino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid using 4-(2-chloroethyl)morpholine hydrochloride as the alkylating agent in Step 1. The product was isolated as a white solid (65 mg, 49.4%). LCMS: m/e 643.6 (MH+), 2.35 min (method 13). 1H NMR (400 MHz, MeOD) δ ppm 7.95 (m, J=8.3 Hz, 2H), 7.24 (m, J=8.3 Hz, 2H), 5.31 (d, J=4.8 Hz, 1H), 4.86 (s, 1H), 4.74 (s, 1H), 3.82-3.99 (m, 4H), 3.37-3.58 (m, 4H), 3.21 (d, J=4.5 Hz, 2H), 3.19 (br. s., 2H), 2.67-2.86 (m, 1H), 2.02-2.26 (m, 5H), 1.83-1.90 (m, 1H), 1.64-1.81 (m, 8H), 1.45-1.64 (m, 7H), 1.34-1.45 (m, 2H), 1.27-1.34 (m, 1H), 1.15-1.27 (m, 4H), 1.12 (s, 3H), 1.04 (s, 3H), 0.99 (s, 3H), 0.93 (s, 3H).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08846647B2uspto-grants-2014_09