Tetrahydrofuran → HCID 50924852, compound

HRID 2179781Notes

Reaction equation

HRID 2179781 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([CH3:41])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:40])[CH2:12][CH2:13][C@@:14]3([C:30](=[O:39])[NH:31][CH:32]4[CH2:36][CH:35]([CH2:37][OH:38])[CH:34]=[CH:33]4)[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:43])[CH3:42])(=O)C.C1COCC1.[OH-].[Na+]>CO>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:41])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:40])[CH2:12][CH2:13][C@@:14]3([C:30]([NH:31][CH:32]4[CH2:36][CH:35]([CH2:37][OH:38])[CH:34]=[CH:33]4)=[O:39])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 50924851HCID 50924851, compound

Product 1

HCID 50924852HCID 50924852, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(4-(hydroxymethyl)cyclopent-2-enylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate (Example 27, 0.22 g) in MeOH:THF (8:8 ml) and cooled the contents to 0° C. then sodium hydroxide (0.05 g in 4 ml water) was added and the contents were stirred for about 6 hours at room temperature then completion of the reaction was monitored by TLC. The reaction mixture was evaporated under reduced pressure, the residue was taken in water and extracted with DCM. The organic layer was 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 (0.14 g) as a white solid. 1H NMR (300 MHz, CDCl3): 0.76-0.99 (m, 16H); 1.25-1.85 (m, 35H); 2.03-2.28 (m, 6H); 2.47 (s, 3H); 2.86-3.10 (m, 3H); 3.18 (s, 1H); 4.60 (s, 1H); 4.74 (s, 1H); ES Mass: 551 (100%), [M+1] 551; HPLC: 96.94%.

Workup

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

Sources & evidence

ORD record
ord-2b55ee55f2db46d5b8474c82494c4ce1
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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