Sodium Hydroxide → HCID 50923383, compound

HRID 2179799Notes

Reaction equation

HRID 2179799 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 50923234HCID 50923234, compound

Product 1

HCID 50923383HCID 50923383, compoundYield 67%

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)-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 43, 0.350 g, 0.517 mmol) in MeOH:THF (2:1) (30 ml) 2N NaOH (10 ml) was added at 0° C. and allowed to stir at room temperature for about 16 hours. After completion of the reaction (monitored by TLC), the volatile was evaporated and the aqueous layer was extracted with ethyl acetate and the organic layer was washed with water, brine and dried over Na2SO4 then the solvent was evaporated and the resulting crude was stirred in hexane and the resulting solid was obtained which was filtered and dried under vacuum to afford the title compound. Wt: 0.220 g: Yield: 67%; 1H NMR (300 MHz, CDCl3): δ 6.27 (d, 1H, J=8.1 Hz), 4.72 (s, 1H), 4.57 (s, 1H), 4.17-4.07 (m, 1H), 3.56-3.11 (m, 4H), 3.19-3.09 (m, 2H), 2.82-2.76 (m, 1H), 2.57-2.43 (m, 1H), 2.39-2.18 (m, 2H), 2.01-1.72 (m, 7H), 1.67 (s, 3H), 1.61-1.11 (m, 22H), 0.96, 0.93, 0.87, 0.81, 0.74 (s, 18H); Mass: [M+1]+ 635 (5%), [M+Na]+ 657 (100%); IR (KBr, cm−1): 3390, 3071, 2947, 2869, 1617, 1455, 1369, 1341, 1250, 1194, 1168, 1108, 1034, 921, 880; M.R: 176.3° C.-180.9° C.; HPLC: 98.9%.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe volatile was evaporated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated
  7. stirringthe resulting crude was stirred in hexane
  8. customthe resulting solid was obtained which
  9. filtrationwas filtered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-9930b1d13d034809a0744ef8d86ead10
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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