HCID 66859977, compound → HCID 58111109, compound

HRID 2179763Notes

Reaction equation

HRID 2179763 reaction equation
C([O:5][C:6]([C@H:8]1[CH2:11][C@@H:10]([C:12]([O:14][C@H:15]2[CH2:32][CH2:31][C@@:30]3([CH3:33])[C@@H:17]([CH2:18][CH2:19][C@:20]4([CH3:44])[C@@H:29]3[CH2:28][CH2:27][C@H:26]3[C@@:21]4([CH3:43])[CH2:22][CH2:23][C@@:24]4([C:40]([OH:42])=[O:41])[CH2:36][CH2:35][C@@H:34]([C:37]([CH3:39])=[CH2:38])[C@@H:25]43)[C:16]2([CH3:46])[CH3:45])=[O:13])[C:9]1([CH3:48])[CH3:47])=[O:7])(C)(C)C>Cl.O1CCOCC1.CCOC(C)=O>[C:6]([C@H:8]1[CH2:11][C@@H:10]([C:12]([O:14][C@H:15]2[CH2:32][CH2:31][C@@:30]3([CH3:33])[C@@H:17]([CH2:18][CH2:19][C@:20]4([CH3:44])[C@@H:29]3[CH2:28][CH2:27][C@H:26]3[C@@:21]4([CH3:43])[CH2:22][CH2:23][C@@:24]4([C:40]([OH:42])=[O:41])[CH2:36][CH2:35][C@@H:34]([C:37]([CH3:39])=[CH2:38])[C@@H:25]43)[C:16]2([CH3:46])[CH3:45])=[O:13])[C:9]1([CH3:48])[CH3:47])([OH:7])=[O:5]

Participants

5

Reactant 1

HCID 66859977HCID 66859977, compound

Product 1

HCID 58111109HCID 58111109, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-((1R,3S)-3-(tert-butoxycarbonyl)-2,2-dimethylcyclobutanecarbonyloxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (Example 3, about 0.160 g, 0.239 mmol) in 2M HCl in Dioxane (10 ml) was stirred at room temperature for about 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with EtOAc and washed with water, the organic layer dried over Na2SO4 and concentrated under reduced pressure. The resulting crude was purified by Silica gel column chromatography (100-200 Mesh, Elution: 20% EtOAc in Hexane) to afford the title compound as a white solid. Wt: 0.086 g; Yield: 59.0%; 1H NMR (300 MHZ, CDCl3): δ 4.74 (s, 1H), 4.61 (s, 1H), 4.47-4.43 (m, 1H), 3.03-2.97 (m, 1H), 2.87-2.74 (m, 2H), 2.63-2.51 (m, 1H), 2.31-2.24 (m, 2H), 2.19-1.90 (m, 3H), 1.69 (s, 3H), 1.78-1.68 (m, 5H), 1.52-1.41 (m, 12H), 1.29-1.02 (m, 9H), 0.97 (s, 3H), 0.93 (s, 3H), 0.85 (s, 9H); Mass: [M+Na]+ 633 (100%); IR (KBr, cm−1): 3427, 2951, 1730, 1706, 1698, 1456, 1376, 1242, 1190, 1107, 1020, 885; M. Range: 282.5-289.3° C.; HPLC: 92.2% % at RT 8.76 minutes.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. washwashed with water
  3. dry with materialthe organic layer dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude was purified by Silica gel column chromatography (100-200 Mesh, Elution: 20% EtOAc in Hexane)

Sources & evidence

ORD record
ord-21ff250a56b8424f978869b0b816343f
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…