Sodium Hydroxide → HCID 66858286, compound

HRID 2179811Notes

Reaction equation

HRID 2179811 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](=[O:48])[NH:31][C@H:32]4[CH2:35][C@@H:34]([C:36]([N:38]5[CH2:43][CH2:42][N:41]([CH2:44][CH3:45])[CH2:40][CH2:39]5)=[O:37])[C:33]4([CH3:47])[CH3:46])[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.[OH-].[Na+]>CO.C1COCC1>[CH2:44]([N:41]1[CH2:42][CH2:43][N:38]([C:36]([C@@H:34]2[CH2:35][C@H:32]([NH:31][C:30]([C@:14]34[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]3[C@@H:16]3[C@@:11]([CH3:49])([CH2:12][CH2:13]4)[C@@:10]4([CH3:50])[C@@H:19]([C@:20]5([CH3:23])[C@@H:7]([CH2:8][CH2:9]4)[C:6]([CH3:51])([CH3:52])[C@@H:5]([OH:4])[CH2:22][CH2:21]5)[CH2:18][CH2:17]3)=[O:48])[C:33]2([CH3:46])[CH3:47])=[O:37])[CH2:39][CH2:40]1)[CH3:45]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66858745HCID 66858745, compound

Product 1

HCID 66858286HCID 66858286, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1S,3R)-3-(4-ethylpiperazine-1-carbonyl)-2,2-dimethylcyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl acetate (Example 66, 0.760 g) in MeOH:THF (2:1) (45 ml) at 0° C., 2N NaOH (15 ml) were added and allowed to stir at room temperature for about 16 hours. After completion of the reaction (monitored by TLC), the volatiles were evaporated, the aqueous layer 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 a white solid. Wt: 0.500 g: Yield: 69.9%; 1H NMR (300 MHz, CDCl3): δ 5.90 (d, J=8.1 Hz, 1H), 4.728 (s, 1H), 4.57 (s, 1H), 4.10 (m, 1H), 3.80-3.41 (m, 4H), 3.20-3.10 (m, 2H), 2.9 (m, 1H), 2.60-2.295 (m, 9H), 2.1 (m, 2H), 1.90 (m, 1H), 1.80-1.02 (m, 22H), 0.95, 0.92 (s, 6H), 0.83 (s, 3H), 0.80 (s, 3H). Mass: [M+H+]+ 679 (100%); IR (KBr, cm−1): 3445, 2946, 2867, 1634, 1459, 1463, 1376, 1270, 1242, 1126, 1043, 983, 883, 768, 656; M.R: 122.0° C.-155.1° C.; HPLC: 94.8%.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe volatiles were evaporated
  3. extractionthe aqueous layer 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-03435f13560e40c296c5e99c28b30221
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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