Sodium Hydroxide → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(cyclopropylmethylamino)-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

HRID 85640노트

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HRID 85640 반응식
[CH:1]1([CH2:4][NH:5][C@:6]23[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:7]2[C@@H:8]2[C@@:21]([CH3:24])([CH2:22][CH2:23]3)[C@@:20]3([CH3:25])[C@@H:11]([C@:12]4([CH3:38])[C@@H:17]([CH2:18][CH2:19]3)[C:16]([CH3:27])([CH3:26])[C:15]([C:28]3[CH:37]=[CH:36][C:31]([C:32]([O:34]C)=[O:33])=[CH:30][CH:29]=3)=[CH:14][CH2:13]4)[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.[OH-].[Na+]>O1CCOCC1>[CH:1]1([CH2:4][NH:5][C@:6]23[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:7]2[C@@H:8]2[C@@:21]([CH3:24])([CH2:22][CH2:23]3)[C@@:20]3([CH3:25])[C@@H:11]([C@:12]4([CH3:38])[C@@H:17]([CH2:18][CH2:19]3)[C:16]([CH3:26])([CH3:27])[C:15]([C:28]3[CH:37]=[CH:36][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=3)=[CH:14][CH2:13]4)[CH2:10][CH2:9]2)[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 68358124methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(cyclopropylmethylamino)-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

생성물 1

HCID 683581044-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(cyclopropylmethylamino)-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 acid수율 27%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
65 °C

실험 절차

To a cloudy mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(cyclopropylmethylamino)-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 (0.024 g, 0.040 mmol) in 1,4-dioxane (1.5 mL) was added NaOH (1N) (0.5 mL, 0.5 mmol). The mixture was heated to 65° C. After two hours, the mixture was cooled to rt and stirred at rt overnight. The mixture was filtered through plug of glass wool and was purified by prep HPLC to afford the title compound (0.007 g, 10.79 μmol, 26.9% yield) as a white film. LCMS: m/e 584.6 (M+H)+, 1.83 min (method 2). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.00 (2H, d, J=8.0 Hz), 7.21 (2H, d, J=8.0 Hz), 5.31 (1H, d, J=5.0 Hz), 4.75 (1H, d, J=1.5 Hz), 4.61 (1H, s), 2.76 (1H, td, J=10.9, 5.6 Hz), 2.62 (1H, dd, J=11.2, 6.1 Hz), 2.23 (1H, dd, J=11.5, 7.8 Hz), 1.97-2.16 (3H, m), 1.82-1.95 (2H, m), 1.70 (3H, s), 1.16 (3H, s), 1.01 (3H, s), 1.00 (3H, s), 0.96 (3H, s), 0.95 (3H, s), 0.80-1.77 (19H, m), 0.48-0.58 (2H, m), 0.09-0.24 (2H, m).

후처리

  1. temperaturethe mixture was cooled to rt
  2. filtrationThe mixture was filtered through plug of glass wool
  3. customwas purified by prep HPLC

출처 및 근거

ORD 기록
ord-41aad92ef52c47eca8bcf6728274f568
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846647B2

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