Sodium Hydroxide → HCID 50924232, compound

HRID 2179813Notes

Reaction equation

HRID 2179813 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 50924231HCID 50924231, compound

Product 1

HCID 50924232HCID 50924232, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1R,3S)-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 69, 550 mg) in MeOH:THF (2:1) at 0° C. temperature 2N NaOH (4 mL) was added and allowed to stir at room temperature for about 16 hours. After completion of the reaction (monitored by TLC), the volatiles was evaporated, 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 the resulting crude was stirred in hexane to get crude solid. The solid crude was purified over silica-gel column chromatography to afford the title compound. Wt: 200 mg, Yield: 93.3%. 1H NMR (300 MHz, CDCl3): δ 5.86 (d, 1H, J=8.1 Hz), 4.72 (s, 1H), 4.57 (s, 1H), 4.18-4.06 (m, 1H), 3.78-3.68 (m, 1H), 3.52-3.30 (m, 3H), 3.23-3.08 (m, 2H), 2.92-2.86 (m, 1H), 2.52-2.20 (m, 3H), 2.01-1.88 (m, 2H), 1.80-1.12 (m, 33H), 0.96, 0.93, 0.87, 0.81, 0.74 (s, 18H); Mass: [M+1]+ 649 (5%), [M+Na]+ 671 (100%); IR (KBr, cm−1): 3353, 2937, 2858, 1635, 1618, 1533, 1459, 1390, 1262, 1250, 1148, 1048, 1033, 1020, 983, 883; M.R: 177° C.-188.7° C.; HPLC: 95.72%.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe volatiles was 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. stirringthe resulting crude was stirred in hexane
  8. customto get crude solid
  9. customThe solid crude was purified over silica-gel column chromatography

Sources & evidence

ORD record
ord-0f0c4bb9c6e949e69df3947a6b8b88a2
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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