Reaktion #172934

ord-280ae93d54f44323be0c59735b64cdc5

Reaktionsgleichung

C=C(C)[C@@H]1CC[C@]2(NCCNS(C)(=O)=O)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-(methylsulfonamido)ethyl)amino)-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
CCCS(=O)(=O)Cl
propane-1-sulfonyl chloride
→
C=C(C)[C@@H]1CC[C@]2(NCCNS(=O)(=O)CCC)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(NCCNS(=O)(=O)CCC)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-1-(prop-1-en-2-yl)-3a-((2-(propylsulfonamido)ethyl)amino)-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

Edukte

C=C(C)[C@@H]1CC[C@]2(NCCNS(C)(=O)=O)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-(methylsulfonamido)ethyl)amino)-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
CCCS(=O)(=O)Cl
propane-1-sulfonyl chloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The title compound was prepared following the method described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(methylsulfonamido)ethyl)amino)-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 propane-1-sulfonyl chloride as the reagent in Step 1. The product was isolated as a white solid (9 mg, 49%). LCMS: m/e 679.48 (M+H)+, 2.34 min (method 11). 1H NMR (500 MHz, CHLOROFORM-d) δ 9.36 (br. s., 1H), 8.00 (d, J=8.4 Hz, 2H), 7.25 (d, J=8.2 Hz, 2H), 6.81 (br. s., 1H), 6.04 (br. s., 1H), 5.31-5.19 (m, 1H), 4.86 (s, 1H), 4.73 (s, 1H), 3.85-3.67 (m, 1H), 3.54 (d, J=14.7 Hz, 1H), 3.38-3.18 (m, 2H), 3.15-3.07 (m, 2H), 2.80 (td, J=11.2, 5.9 Hz, 1H), 2.26-0.95 (m, 24H), 1.71 (s, 3H), 1.20 (s, 3H), 1.12 (t, J=7.4 Hz, 3H), 1.05 (s, 3H), 0.97 (s, 3H), 0.96 (s, 3H), 0.94 (s, 3H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846647B2uspto-grants-2014_09