Diisopropylethylamine → HCID 67774684、化合物

HRID 406883

反応式

HRID 406883 の反応式
[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]

参加物

6

反応物 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

生成物 1

HCID 67774684HCID 67774684、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

出典と根拠

ORDレコード
ord-cc77223c4dab46a4a9dae5cb37ac5740
出典データセット
uspto-grants-2014_06
特許番号
US08754068B2

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