Succinic anhydride → 4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[(4-hydroxy-4-oxo-butanoyl)amino]methyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid

HRID 405097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405097
[NH2:1][CH2:2][C@:3]12[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:4]1[C@@H:5]1[C@@:18]([CH3:21])([CH2:19][CH2:20]2)[C@@:17]2([CH3:22])[C@@H:8]([C@:9]3([CH3:34])[C@@H:14]([CH2:15][CH2:16]2)[C:13]([CH3:24])([CH3:23])[C:12]([C:25]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1.[O:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:42]([CH2:43][CH2:44][C:45]([NH:1][CH2:2][C@:3]12[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:4]1[C@@H:5]1[C@@:18]([CH3:21])([CH2:19][CH2:20]2)[C@@:17]2([CH3:22])[C@@H:8]([C@:9]3([CH3:34])[C@@H:14]([CH2:15][CH2:16]2)[C:13]([CH3:24])([CH3:23])[C:12]([C:25]2[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1)=[O:46])([OH:47])=[O:41]

Komponenten

6

Edukt 3

HCID 7922Succinic anhydrideHCID 81531DiisopropylethylamineHCID 715977424-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aminomethyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid

Produkt 1

HCID 715967764-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[(4-hydroxy-4-oxo-butanoyl)amino]methyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acidAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aminomethyl)-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 (20 mg, 0.037 mmol) in DCM (2 ml) was added dihydrofuran-2,5-dione (11.04 mg, 0.110 mmol) followed by DMAP (4.49 mg, 0.037 mmol) and DIPEA (6.42 μl, 0.037 mmol). The mixture was stirred at rt for 18 h. The solvent was removed in vacuo and the resulting residue was purified by prep. HPLC. The product was isolated as a white solid (5 mg, 21.1%). LCMS: m/e 644.5 (MH+), 2.80 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 7.94 (d, J=8.5 Hz, 2H), 7.16-7.34 (m, 2H), 5.32 (dd, J=6.4, 1.6 Hz, 1H), 4.74 (d, J=2.0 Hz, 1H), 4.62 (s, 1H), 3.54 (d, J=13.6 Hz, 1H), 3.04 (d, J=13.8 Hz, 1H), 2.57-2.71 (m, 2H), 2.44-2.57 (m, 2H), 2.17 (dd, J=17.2, 6.4 Hz, 1H), 2.09 (dd, J=13.1, 1.8 Hz, 1H), 1.85 (dd, J=12.2, 3.4 Hz, 2H), 1.65-1.82 (m, 8H), 1.61 (br. s., 2H), 1.53 (d, J=10.5 Hz, 3H), 1.48 (d, J=2.0 Hz, 1H), 1.35-1.45 (m, 3H), 1.24-1.35 (m, 3H), 1.16-1.24 (m, 4H), 1.02-1.16 (m, 8H), 0.99 (s, 3H), 0.95 (s, 3H).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-af9f15ba4c7144eca5b87237a697b2c4
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748415B2

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