Pyridine → HCID 50925001, compound

HRID 2179824Notes

Reaction equation

HRID 2179824 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:45])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:44])[CH2:9][CH2:10][C@@:11]3([C:27]([C@@H:29]4[CH2:33][CH2:32][C@H:31]([CH2:34][N:35]5[CH2:40][CH2:39][CH:38]([C:41]([OH:43])=[O:42])[CH2:37][CH2:36]5)[CH2:30]4)=[O:28])[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]32)[C:3]1([CH3:47])[CH3:46].N1C=CC=CC=1.[CH3:54][C:55]1([CH3:62])[CH2:59][C:58](=[O:60])[O:57][C:56]1=[O:61]>C(OCC)(=O)C>[C:56]([C:55]([CH3:62])([CH3:54])[CH2:59][C:58]([O:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:45])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:44])[CH2:9][CH2:10][C@@:11]3([C:27]([C@@H:29]4[CH2:33][CH2:32][C@H:31]([CH2:34][N:35]5[CH2:36][CH2:37][CH:38]([C:41]([OH:43])=[O:42])[CH2:39][CH2:40]5)[CH2:30]4)=[O:28])[CH2:23][CH2:22][C@@H:21]([C:24]([CH3:26])=[CH2:25])[C@@H:12]32)[C:3]1([CH3:47])[CH3:46])=[O:60])([OH:61])=[O:57]

Participants

5

Reactant 3

HCID 1049PyridineHCID 870672,2-Dimethylsuccinic anhydrideHCID 66858254HCID 66858254, compound

Product 1

HCID 50925001HCID 50925001, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-(((1S,3R)-3-((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)cyclopentyl)methyl)piperidine-4-carboxylic acid (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 and 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, then 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: 778 (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
  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-3a527f7936c84818a52df91b69af20bd
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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