Sodium Hydroxide → HCID 50923233, compound

HRID 2179795Notes

Reaction equation

HRID 2179795 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([CH3:52])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:51])[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]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:41]([O:43]C)=[O:42])=[O:38])[C:34]4([CH3:50])[CH3:49])=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:54])[CH3:53])(=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([CH3:52])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:51])[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]([CH2:45][CH:46]([CH3:47])[CH3:48])[C:41]([OH:43])=[O:42])=[O:38])[C:34]4([CH3:50])[CH3:49])=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:53])[CH3:54]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50923232HCID 50923232, compound

Product 1

HCID 50923233HCID 50923233, compoundYield 56.7%

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)-4-methylpentanoate (Example 41, 0.190 g, 0.253 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 volatiles were evaporated and the reaction mixture was acidified with 1N HCl, extracted with EtOAc, dried over Na2SO4 then the organic layer was concentrated and dried under vacuum to afford the title compound as an off white solid. Wt: 0.100 g: Yield: 56.7%; 1H NMR (300 MHz, DMSO-d6): δ 7.69 (d, 1H, J=8.1 Hz), 7.54 (d, 1H, J=6.6 Hz), 4.62 (s, 1H), 4.51 (s, 1H), 4.29-4.18 (m, 2H), 3.95-3.84 (m, 1H), 3.01-2.88 (m, 2H), 2.34-2.18 (m, 3H), 1.91-1.72 (m, 3H), 1.69-1.10 (m, 31H), 0.96-0.58 (m, 23H); Mass: [M+1]+694 (10%), [M+Na]+ 717 (100%); IR (KBr, cm−1): 3454, 2950, 1726, 1634, 1523, 1466, 1369, 1266, 1207, 1195, 1157, 1044, 1009, 922, 882, 722; M.R: 192.4° C.-213.8° C.; HPLC: 95.97%.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe volatiles were evaporated
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationthe organic layer was concentrated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-714ce9c59e0d4443a613f7af4ac46ef3
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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