Sodium Hydroxide → HCID 50923931, compound

HRID 2179766Notes

Reaction equation

HRID 2179766 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([CH3:48])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:47])[CH2:12][CH2:13][C@@:14]3([C:30](=[O:46])[NH:31][C@H:32]4[CH2:35][C@@H:34]([C:36]([N:38]5[CH2:43][CH2:42][O:41][CH2:40][CH2:39]5)=[O:37])[C:33]4([CH3:45])[CH3:44])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:50])[CH3:49])(=O)C.[OH-].[Na+]>CO.C1COCC1>[CH3:44][C:33]1([CH3:45])[C@H:34]([C:36]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[O:37])[CH2:35][C@@H:32]1[NH:31][C:30]([C@:14]12[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]1[C@@H:16]1[C@@:11]([CH3:47])([CH2:12][CH2:13]2)[C@@:10]2([CH3:48])[C@@H:19]([C@:20]3([CH3:23])[C@@H:7]([CH2:8][CH2:9]2)[C:6]([CH3:49])([CH3:50])[C@@H:5]([OH:4])[CH2:22][CH2:21]3)[CH2:18][CH2:17]1)=[O:46]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50923930HCID 50923930, compound

Product 1

HCID 50923931HCID 50923931, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1S,3R)-2,2-dimethyl-3-(morpholine-4-carbonyl)cyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate (Example 7, 0.380 g, 0.55 mmol) in MeOH:THF (2:1) (6 ml) NaOH (2N, 2 ml) was added at about 0° C. and allowed to stir at room temperature for about 16 hours. After completion of the reaction (monitored by TLC) the volatiles was evaporated and the aqueous layer was extracted with ethyl acetate and dried with Na2SO4. The solvent was evaporated and purified by silica gel column (100-200 mesh, elution 15% EtOAc in hexane) to afford the title compound as an off white solid. Wt: 0.320 g: Yield: 89.6%; 1H NMR (300 MHz, CDCl3): δ 5.88 (d, 1H, J=8.1 Hz), 4.73 (s, 1H), 4.58 (s, 1H), 4.18-4.07 (m, 1H), 3.80-3.41 (m, 7H), 3.21-3.08 (m, 2H), 2.91-2.83 (m, 1H), 2.50-2.29 (m, 3H), 1.98-1.87 (m, 2H), 1.80-1.10 (m, 26H), 0.95-0.92 (s, 12H), 0.99-0.68 (s, 9H); Mass: [M+1]+ 651 (100%), [M+Na]+ 673 (70%); IR (KBr, cm−1): 3367, 2856, 2926, 1714, 1634, 1493, 1463, 1375, 1270, 1241, 1115, 1040, 983, 884, 756, 665; M.R: 262.5° C.-267.8° C.; HPLC: 90.7%.

Workup

  1. customAfter completion of the reaction (monitored by TLC) the volatiles
  2. customwas evaporated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried with Na2SO4
  5. customThe solvent was evaporated
  6. custompurified by silica gel column (100-200 mesh, elution 15% EtOAc in hexane)

Sources & evidence

ORD record
ord-7a57f2e0759d463bb4dcbfab305f3a78
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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