Sodium Hydroxide → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(furan-2-ylmethylamino)-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 85644노트

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HRID 85644 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C@:8]12[CH2:43][CH2:42][C@@H:41]([C:44]([CH3:46])=[CH2:45])[C@@H:9]1[C@@H:10]1[C@@:23]([CH3:26])([CH2:24][CH2:25]2)[C@@:22]2([CH3:27])[C@@H:13]([C@:14]3([CH3:40])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1.[OH-].[Na+]>O1CCOCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C@:8]12[CH2:43][CH2:42][C@@H:41]([C:44]([CH3:46])=[CH2:45])[C@@H:9]1[C@@H:10]1[C@@:23]([CH3:26])([CH2:24][CH2:25]2)[C@@:22]2([CH3:27])[C@@H:13]([C@:14]3([CH3:40])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 86676601methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(furan-2-ylmethylamino)-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 683581384-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(furan-2-ylmethylamino)-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 60.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

To a solution of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(furan-2-ylmethylamino)-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 (31 mg, 0.050 mmol) in 1,4-dioxane (2 mL) was added 1N NaOH (0.248 mL, 0.248 mmol). The mixture was heated to 85° C. for 22 h then was cooled to rt. The crude product was purified by prep HPLC. The fractions containing the expected product were combined and were concentrated under reduced pressure to afford the title compound (19.3 mg, 0.030 mmol, 60.5% yield) as a clear film. LCMS: m/e 610.69 (M+H)+, 2.35 min (method 2). 1H NMR (400 MHz, CHLOROFORM-d) d ppm 8.00 (d, J=7.78 Hz, 2H), 7.37 (d, J=1.00 Hz, 1H), 7.23 (d, J=7.78 Hz, 2H), 6.33 (dd, J=3.14, 1.88 Hz, 1H), 6.21 (d, J=2.76 Hz, 1H), 5.53 (br. s., 1H), 5.29-5.34 (m, 1H), 4.72 (d, J=1.76 Hz, 1H), 4.60 (s, 1H), 3.67 (s, 2H), 2.64 (td, J=10.85, 5.40 Hz, 1H), 1.71 (s, 3H), 1.10-1.15 (m, 3H), 1.01 (s, 3H), 1.00 (s, 3H), 0.97-2.18 (m, 22H), 0.96 (s, 6H).

후처리

  1. temperaturethen was cooled to rt
  2. customThe crude product was purified by prep HPLC
  3. additionThe fractions containing the expected product
  4. concentrationwere concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-610cdb74e282475a9e5b26353f8d70fe
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846647B2

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