Tetrahydrofuran → HCID 66858586, compound

HRID 2179810Notes

Reaction equation

HRID 2179810 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:51])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:50])[CH2:12][CH2:13][C@@:14]3([C:30]([CH:32]4[CH2:37][CH2:36][C:35]([CH2:43][C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:34][CH2:33]4)=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:53])[CH3:52])(=O)C.C1COCC1.[OH-].[Na+]>CO>[CH2:43]([C:35]1([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:36][CH2:37][CH:32]([C:30]([C@:14]23[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]2[C@@H:16]2[C@@:11]([CH3:50])([CH2:12][CH2:13]3)[C@@:10]3([CH3:51])[C@@H:19]([C@:20]4([CH3:23])[C@@H:7]([CH2:8][CH2:9]3)[C:6]([CH3:52])([CH3:53])[C@@H:5]([OH:4])[CH2:22][CH2:21]4)[CH2:18][CH2:17]2)=[O:31])[CH2:33][CH2:34]1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66858412HCID 66858412, compound

Product 1

HCID 66858586HCID 66858586, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carbonyl)-1-benzylcyclohexanecarboxylate (Example 55, 0.9 g) was taken in MeOH:THF (8:8 ml) and cooled the contents to 0° C. then sodium hydroxide (0.28 g in 4 ml water) was added and stirred for about 6 hours at room temperature. Completion of the reaction was monitored by TLC. The reaction mixture was evaporated under reduced pressure and the residue was taken in water, extracted with DCM, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% methanol in DCM as eluent to furnish the title compound (0.45 g) as a white solid. 1H NMR (300 MHz, CDCl3): 0.57-0.97 (m, 19H); 1.18-1.21 (m, 8H); 1.25-1.41 (m, 12H); 1.49-1.62 (m, 8H); 1.65-1.82 (m, 10H); 1.85-1.98 (m, 4H); 2.56-2.69 (m, 2H); 3.29-3.38 (m, 1H); 3.89-3.90 (m, 1H); 4.12-4.23 (m, 2H) 4.56 (s, 1H); 4.71 (s, 1H); 7.03-7.05 (m, 2H); 7.23-7.25 (m, 3H); MASS: 685 (100%).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ca0494d94e5f49b881088391de20c22e
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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