Sodium Hydroxide → HCID 50923078, compound

HRID 2179792Notes

Reaction equation

HRID 2179792 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([CH3:51])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:50])[CH2:12][CH2:13][C@@:14]3([C:30]([NH:32][C@@H:33]4[CH2:36][C@H:35]([C:37]([NH:39][C@@H:40]([CH:45]([CH3:47])[CH3:46])[C:41]([O:43]C)=[O:42])=[O:38])[C:34]4([CH3:49])[CH3:48])=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:53])[CH3:52])(=O)C.[OH-].[Na+]>CO.C1COCC1>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:51])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:50])[CH2:12][CH2:13][C@@:14]3([C:30]([NH:32][C@@H:33]4[CH2:36][C@H:35]([C:37]([NH:39][C@@H:40]([CH:45]([CH3:46])[CH3:47])[C:41]([OH:43])=[O:42])=[O:38])[C:34]4([CH3:49])[CH3:48])=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:52])[CH3:53]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50923077HCID 50923077, compound

Product 1

HCID 50923078HCID 50923078, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-methyl 2-((1S,3R)-3-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetoxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxamido)-2,2-dimethylcyclobutanecarboxamido)-3-methylbutanoate (Example 39, 0.300 g, 0.407 mmol) in MeOH:THF (2:1) (7.5 ml) 2N NaOH (2.5 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 reaction mixture was acidified with 1N HCl, filtered, washed with water and dried under vacuum to afford the title compound as an off white solid. Wt: 0.180 g: Yield: 64.9%; 1H NMR (300 MHz, DMSO-d6): δ 7.55 (d, 2H, J=6.6 Hz), 4.62 (s, 1H), 4.51 (s, 1H), 4.20-4.11 (m, 1H), 3.91-3.82 (m, 1H), 3.00-2.98 (m, 2H), 2.71-2.56 (m, 1H), 2.48-2.39 (m, 1H), 2.37-2.18 (m, 2H), 1.92-1.76 (m, 2H), 1.69-1.15 (m, 32H), 0.93-0.76 (m, 15H), 0.85 (s, 3H), 0.84 (s, 3H); Mass: [M+Na]+ 703 (100); IR (KBr, cm−1): 3321, 2951, 1713, 1631, 1532, 1460, 1386, 1252, 1169, 1108, 1044, 983, 882; M.R: 203.9° C.-205.0° C.; HPLC: 97.3%.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe volatile was evaporated
  3. filtrationfiltered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6c3cb3350f864abe832767465947fd89
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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