Pyridine → HCID 50925000, compound

HRID 2179823Notes

Reaction equation

HRID 2179823 reaction equation
[CH2:1]([C:3]1([C:41]([OH:43])=[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.[CH3:50][C:51]1([CH3:58])[CH2:55][C:54](=[O:56])[O:53][C:52]1=[O:57]>C(OCC)(=O)C>[C:52]([C:51]([CH3:58])([CH3:50])[CH2:55][C:54]([O:33][C@H:20]1[CH2:19][CH2:18][C@@:17]2([CH3:34])[C@@H:22]([CH2:23][CH2:24][C@:25]3([CH3:30])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:26]3([CH3:29])[CH2:27][CH2:28][C@@:11]3([C:9]([N:6]4[CH2:5][CH2:4][C:3]([CH2:1][CH3:2])([C:41]([OH:43])=[O:42])[CH2:8][CH2:7]4)=[O:10])[CH2:37][CH2:36][C@@H:35]([C:38]([CH3:40])=[CH2:39])[C@@H:12]32)[C:21]1([CH3:32])[CH3:31])=[O:56])([OH:57])=[O:53]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870672,2-Dimethylsuccinic anhydrideHCID 509249994-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-carboxylic acid

Product 1

HCID 50925000HCID 50925000, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 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-carboxylic acid (Example 84, 0.5 g, 0.80 mmol) in pyridine (5 ml) dimethyl amino pyridine (0.2 g, 1.6 mmol) and 3,3-dimethyldihydrofuran-2,5-dione (0.82 ml) were added. The contents were refluxed for about 16 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with ethyl acetate (30 ml). The organic layer was washed with 5% aqueous HCl, water followed by brine then 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: 725 (100%), [M+1].

Workup

  1. temperatureThe contents were refluxed for about 16 hours
  2. customAfter completion of the reaction (monitored by TLC)
  3. washThe organic layer was washed with 5% aqueous HCl, water
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b695a92c159456b87d95b4b1d3da01a
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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