Sodium Hydroxide → HCID 50924230, compound

HRID 2179772Notes

Reaction equation

HRID 2179772 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([CH3:47])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:46])[CH2:12][CH2:13][C@@:14]3([C:30](=[O:45])[NH:31][C@H:32]4[CH2:35][C@@H:34]([C:36]([N:38]5[CH2:42][CH2:41][CH2:40][CH2:39]5)=[O:37])[C:33]4([CH3:44])[CH3:43])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:49])[CH3:48])(=O)C.[OH-].[Na+]>CO.C1COCC1>[CH3:43][C:33]1([CH3:44])[C@H:34]([C:36]([N:38]2[CH2:39][CH2:40][CH2:41][CH2:42]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]([CH3:46])([CH2:12][CH2:13]2)[C@@:10]2([CH3:47])[C@@H:19]([C@:20]3([CH3:23])[C@@H:7]([CH2:8][CH2:9]2)[C:6]([CH3:48])([CH3:49])[C@@H:5]([OH:4])[CH2:22][CH2:21]3)[CH2:18][CH2:17]1)=[O:45]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50924229HCID 50924229, compound

Product 1

HCID 50924230HCID 50924230, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1S,3R)-2,2-dimethyl-3-(pyrrolidine-1-carbonyl)cyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate (Example 13, 0.230 g, 0.340 mmol) in MeOH:THF (2:1) (9 ml) NaOH (2N, 3 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 were evaporated and the aqueous layer was extracted with ethyl acetate and the organic layer was washed with water, brine 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: 0.150 g: Yield: 69.5%; 1H NMR (300 MHz, CDCl3): δ 6.39 (d, 1H, J=8.4 Hz), 4.73 (s, 1H), 4.57 (s, 1H), 4.13-4.03 (m, 1H), 3.58-3.28 (m, 4H), 3.21-3.07 (m, 2H), 2.79 (t, 1H, J=7.2 Hz), 2.57-2.33 (m, 2H), 2.27-2.18 (m, 1H), 2.04-1.72 (m, 8H), 1.70-1.10 (m, 23H), 0.95, 0.92, 0.88, 0.83, 0.80, 0.75 (s, 21H); Mass: [M+1]+ 635 (100%), [M+Na]+ 657 (90%); IR (KBr, cm−1): 3489, 2947, 2869, 1637, 1615, 1441, 1376, 1357, 1250, 1194, 1050, 881, 717; M.R: 172.4° C.-173.8° C.; HPLC: 96.79%.

Workup

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

Sources & evidence

ORD record
ord-0b8ede54ac2b492c99d799f8a7a8f4b7
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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