HCID 54759583, 화합물 → 4-[(1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropyl-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 406890노트

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HRID 406890 반응식
[OH: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>CO.C(OCC)(=O)C.[Pd]>[OH:1][CH2:2][C@:3]12[CH2:37][CH2:36][C@@H:35]([CH:38]([CH3:40])[CH3:39])[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

참가 물질

5

반응물 1

HCID 54759583HCID 54759583, 화합물

생성물 1

HCID 547606924-[(1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropyl-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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(hydroxymethyl)-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 (50 mg, 0.092 mmol) and a catalytic amount of Pd/C (9.77 mg, 0.092 mmol) was dissolved in a mixture of methanol (1 mL) and ethyl acetate (1 mL) and stirred under 1 ATM of H2 for 24 hours. LCMS indicated the completion of the reaction. The reaction mixture was filtered to remove the catalyst. The solution was concentrated in vacuo and the residue was purified using reverse phase prep HPLC to afford the title compound as a white solid. LCMS: m/e 529.29 (M+H−H2O)+, 0.15 min (method 1). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 0.80 (d, 3H), 0.88 (d, J=6.71 Hz, 3H), 0.97 (s, 6H), 1.02 (s, 6H), 1.12 (s, 3H), 1.18-2.23 (m, 24H), 3.36 (d, J=10.99 Hz, 1H), 3.84 (d, J=10.68 Hz, 1H), 5.27-5.42 (m, 1H), 7.26 (d, J=7.93 Hz, 2H), 8.01 (d, J=8.24 Hz, 2H).

후처리

  1. customthe completion of the reaction
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationThe solution was concentrated in vacuo
  5. customthe residue was purified

출처 및 근거

ORD 기록
ord-4b5ff54c115441f5baee7ea7c82e2583
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754068B2

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