Diisopropylethylamine → HCID 67774684, Verbindung

HRID 406883

Reaktionsgleichung

Reaktionsgleichung von HRID 406883
[CH3:1][CH:2]([S:4]([NH2:7])(=[O:6])=[O:5])[CH3:3].CCN(C(C)C)C(C)C.Cl[C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:27]([CH3:64])([CH3:63])[C@H:28]3[C@:41]([CH3:44])([CH2:42][CH:43]=2)[CH:40]2[C@:31]([CH3:62])([C@@:32]4([CH3:61])[C@H:37]([CH2:38][CH2:39]2)[C@H:36]2[C@H:45]([C:48]([CH3:50])=[CH2:49])[CH2:46][CH2:47][C@:35]2([C:51]([O:53]CC2C=CC=CC=2)=[O:52])[CH2:34][CH2:33]4)[CH2:30][CH2:29]3)=[CH:22][CH:21]=1)=[O:19]>CN(C1C=CN=CC=1)C.COCCOC>[CH:2]([S:4]([NH:7][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:27]([CH3:64])([CH3:63])[C@H:28]3[C@:41]([CH3:44])([CH2:42][CH:43]=2)[CH:40]2[C@:31]([CH3:62])([C@@:32]4([CH3:61])[C@H:37]([CH2:38][CH2:39]2)[C@H:36]2[C@H:45]([C:48]([CH3:50])=[CH2:49])[CH2:46][CH2:47][C@:35]2([C:51]([OH:53])=[O:52])[CH2:34][CH2:33]4)[CH2:30][CH2:29]3)=[CH:22][CH:21]=1)=[O:19])(=[O:6])=[O:5])([CH3:3])[CH3:1]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 3549191Propane-2-sulfonamideHCID 86666259(1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-benzyl 9-(4-(chlorocarbonyl)phenyl)-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]chrysene-3a-carboxylate

Produkt 1

HCID 67774684HCID 67774684, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a mixture of propane-2-sulfonamide (18.46 mg, 0.150 mmol), DMAP (0.915 mg, 7.49 μmol) and Hunig's Base (0.065 mL, 0.375 mmol) in DME (2 mL) was added (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-benzyl 9-(4-(chlorocarbonyl)phenyl)-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]chrysene-3a-carboxylate (50 mg, 0.075 mmol). The reaction mixture was stirred for 16 hours. LCMS indicated the formation of the desired product. The reaction mixture was quenched with distilled water, extracted with ethyl acetate and concentrated under reduced pressure to give crude intermediate (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-benzyl 9-(4-(isopropylsulfonylcarbamoyl)phenyl)-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]chrysene-3a-carboxylate as a yellow solid. LCMS: m/e 754.60 (M+H)+, 2.36 min (method 7). To this intermediate (50 mg, 0.066 mmol) in EtOAc (2 mL) and MeOH (2.00 mL) was added 10% Pd/C (21.17 mg, 0.020 mmol). The reaction mixture was hydrogentated using a Parr shaker at 40 Psi for 17 hours. LCMS indicated the reaction was completed. The reaction mixture was filtered through a pad of celite and concentrated under reduced. The residue was purified by prep HPLC to provide the desired product, (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-9-(4-(isopropylsulfonylcarbamoyl)phenyl)-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]chrysene-3a-carboxylic acid, as a white solid (12 mg, 26%). LCMS: m/e 664.48 (M+H)+, 2.18 min (method 7). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 0.91 (s, 6H), 0.96 (s, 3H), 1.00 (d, J=4.27 Hz, 6H), 1.18-1.27 (m, 8H), 1.35-1.55 (m, 13H), 1.60-1.75 (m, 5H), 1.94-2.03 (m, 2H), 2.07-2.14 (m, 1H), 2.22-2.31 (m, 2H), 2.97-3.07 (m, 1H), 3.98-4.08 (m, 1H), 4.61 (s, 1H), 4.74 (s, 1H), 5.28 (d, J=4.88 Hz, 1H), 7.23-7.25 (m, 2H), 7.74 (d, J=8.24 Hz, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-cc77223c4dab46a4a9dae5cb37ac5740
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754068B2

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