Pyridine → HCID 50924391, compound

HRID 2179815Notes

Reaction equation

HRID 2179815 reaction equation
[CH2:1]([C:3]1([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:8][CH2:7][N:6]([C:9]([C@:11]23[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:12]2[C@@H:13]2[C@@:26]([CH3:29])([CH2:27][CH2:28]3)[C@@:25]3([CH3:30])[C@@H:16]([C@:17]4([CH3:34])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:32])([CH3:31])[C@@H:20]([OH:33])[CH2:19][CH2:18]4)[CH2:15][CH2:14]2)=[O:10])[CH2:5][CH2:4]1)[CH3:2].N1C=CC=CC=1.[CH3:52][C:53]1([CH3:60])[CH2:57][C:56](=[O:58])[O:55][C:54]1=[O:59]>C(OCC)(=O)C>[CH2:44]([O:43][C:41]([C:3]1([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]([C:9]([C@:11]23[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:12]2[C@@H:13]2[C@@:26]([CH3:29])([CH2:27][CH2:28]3)[C@@:25]3([CH3:30])[C@@H:16]([C@:17]4([CH3:34])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:32])([CH3:31])[C@@H:20]([O:33][C:56](=[O:58])[CH2:57][C:53]([CH3:60])([CH3:52])[C:54]([OH:59])=[O:55])[CH2:19][CH2:18]4)[CH2:15][CH2:14]2)=[O:10])[CH2:7][CH2:8]1)=[O:42])[CH3:45]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870672,2-Dimethylsuccinic anhydrideHCID 50924390HCID 50924390, compound

Product 1

HCID 50924391HCID 50924391, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 4-ethyl-1-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carbonyl)piperidine-4-carboxylate (Example 73, 0.5 g, 0.80 mmol) in pyridine (5 ml) dimethyl amino pyridine (0.2 g, 1.6 mmol) was added then 3,3-dimethyldihydrofuran-2,5-dione (0.82 ml) was added and the contents were refluxed for about 16 hours. Completion of the reaction was monitored by TLC, the reaction mixture was diluted with ethyl acetate (30 ml) and the organic layer was washed with 5% aqueous HCl, washed with water followed by brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% MeOH in DCM as eluent to furnish the title compound (0.25 g) as a white solid. 1H NMR (300 MHz, CDCl3): 0.95-1.16 (m, 19H); 1.23-1.78 (m, 23H); 2.15-2.59 (m, 11H); 2.77-3.58 (m, 16H); 4.33-4.70 (m, 4H); 5.58-5.60 (s, 1H); 5.78-5.80 (s, 1H); 7.44-7.47 (s, 1H); ES Mass: 753; (100%), [M+1].

Workup

  1. temperaturethe contents were refluxed for about 16 hours
  2. washthe organic layer was washed with 5% aqueous HCl
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6cf7032394e14dcc8dd53cdef50bd9d7
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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