반응 #172776

ord-1e27660451b74408bf8bea8731fc5d42

반응 방정식

C=C(C)[C@@H]1CC[C@]2(NC(=O)CCN(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-(3-(dimethylamino)propanamido)-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
CS(=O)(=O)N1CCCC1C(=O)O
1-(methylsulfonyl)pyrrolidine-2-carboxylic acid
C=C(C)[C@@H]1CC[C@]2(N)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(c6ccc(C(=O)OC)cc6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-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)benzoate
→
C=C(C)[C@@H]1CC[C@]2(NC(=O)C3CCCN3S(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
title compound
수율 17.0%
C=C(C)[C@@H]1CC[C@]2(NC(=O)C3CCCN3S(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-(1-(methylsulfonyl)pyrrolidine-2-carboxamido)-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
수율 17.0%

반응물

C=C(C)[C@@H]1CC[C@]2(NC(=O)CCN(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-(3-(dimethylamino)propanamido)-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
CS(=O)(=O)N1CCCC1C(=O)O
1-(methylsulfonyl)pyrrolidine-2-carboxylic acid
C=C(C)[C@@H]1CC[C@]2(N)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(c6ccc(C(=O)OC)cc6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-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)benzoate

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타m/e 705.5 (M+H)+, 2.04 min (method 6)

실험 절차

The title compound was prepared in 17% yield from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-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)benzoate following the same procedure as described for the preparation of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(dimethylamino)propanamido)-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, except 1-(methylsulfonyl)pyrrolidine-2-carboxylic acid was used instead of 3-(dimethylamino)propionic acid hydrochloride in Step 1. LCMS: m/e 705.5 (M+H)+, 2.04 min (method 6). 1H NMR (500 MHz, 1:1 CDCl3:MeOD) δ=7.92 (d, J=8.5 Hz, 2H), 7.20 (d, J=8.2 Hz, 2H), 6.88 (s, 1H), 5.29 (dd, J=1.5, 6.1 Hz, 1H), 4.76 (d, J=1.5 Hz, 1H), 4.10 (dd, J=3.1, 8.8 Hz, 1H), 3.60 (ddd, J=3.5, 7.0, 10.2 Hz, 1H), 3.40 (dt, J=6.4, 9.6 Hz, 1H), 2.96 (s, 3H), 2.62-2.52 (m, 2H), 2.42 (dd, J=8.2, 11.6 Hz, 1H), 2.31 (dddd, J=3.2, 3.4, 6.4, 9.7 Hz, 1H), 2.21-2.16 (m, 1H), 2.16-2.10 (m, 1H), 2.03 (tdd, J=3.2, 6.6, 13.0 Hz, 1H), 1.99-1.89 (m, 2H), 1.82-1.75 (m, 1H), 1.75-1.72 (m, 1H), 1.70 (s, 3H), 1.69-1.66 (m, 1H), 1.58-1.46 (m, 6H), 1.46-1.29 (m, 5H), 1.28-1.22 (m, 1H), 1.14 (d, J=13.1 Hz, 2H), 1.09 (s, 3H), 1.03 (s, 3H), 1.01 (s, 3H), 0.93 (s, 6H).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08846647B2uspto-grants-2014_09