반응 #172774

ord-f3bd457855f34740b2f3bfd95635f570

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
O=C(O)CN1C(=O)OC[C@@H]1c1ccccc1
(S)-(+)-2-oxo-4-phenyl-3-oxazolidineacetic 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)CN3C(=O)OC[C@@H]3c3ccccc3)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 30.0%
C=C(C)[C@@H]1CC[C@]2(NC(=O)CN3C(=O)OC[C@@H]3c3ccccc3)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-((S)-2-oxo-4-phenyloxazolidin-3-yl)acetamido)-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 30.0%

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
O=C(O)CN1C(=O)OC[C@@H]1c1ccccc1
(S)-(+)-2-oxo-4-phenyl-3-oxazolidineacetic 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 733.5 (M+H)+, 2.25 min (method 6)

실험 절차

The title compound was prepared in 30% 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 (S)-(+)-2-oxo-4-phenyl-3-oxazolidineacetic acid was used instead of 3-(dimethylamino)propionic acid hydrochloride in Step 1. LCMS: m/e 733.5 (M+H)+, 2.25 min (method 6). 1H NMR (400 MHz, 1:1 CDCl3:MeOD) δ=7.92 (d, J=8.3 Hz, 2H), 7.47-7.39 (m, 3H), 7.37-7.32 (m, 2H), 7.20 (d, J=8.3 Hz, 2H), 6.60 (s, 1H), 5.28 (d, J=4.5 Hz, 1H), 5.04 (t, J=8.3 Hz, 1H), 4.75 (t, J=8.9 Hz, 1H), 4.71 (s, 1H), 4.61 (br. s., 1H), 4.25-4.19 (m, 1H), 4.04 (d, J=16.3 Hz, 1H), 3.40 (d, J=16.3 Hz, 1H), 2.65-2.59 (m, 1H), 2.47 (dt, J=4.8, 11.0 Hz, 1H), 2.37 (dd, J=8.2, 11.7 Hz, 1H), 2.11 (dd, J=6.3, 17.1 Hz, 1H), 1.84-1.70 (m, 4H), 1.69 (s, 3H), 1.66-1.59 (m, 1H), 1.58-1.40 (m, 7H), 1.39-1.22 (m, 6H), 1.09 (br. s., 1H), 1.07 (s, 3H), 1.00 (s, 6H), 0.95 (s, 3H), 0.94 (br. s., 3H).

출처

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