Tetrahydrofuran → HCID 50924849, compound

HRID 2179779Notes

Reaction equation

HRID 2179779 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([CH3:50])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:49])[CH2:12][CH2:13][C:14]3([C:30]([N:32]4[CH:37]5[CH2:38][CH2:39][CH:33]4[CH2:34][CH:35]([N:40]4[C:44]([CH3:45])=[N:43][N:42]=[C:41]4[CH:46]([CH3:48])[CH3:47])[CH2:36]5)=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:52])[CH3:51])(=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([CH3:50])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:49])[CH2:12][CH2:13][C:14]3([C:30]([N:32]4[CH:33]5[CH2:39][CH2:38][CH:37]4[CH2:36][CH:35]([N:40]4[C:44]([CH3:45])=[N:43][N:42]=[C:41]4[CH:46]([CH3:47])[CH3:48])[CH2:34]5)=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:51])[CH3:52]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 50924697HCID 50924697, compound

Product 1

HCID 50924849HCID 50924849, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane-8-carbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate (Example 22, 0.2 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 for about 6 hours at room temperature and 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: [M+] 672 (100%), [M+1] 673; HPLC: 95.5%.

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-1721b422448b4c699b81cc610431b789
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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