HCID 50925293, compound → HCID 50923076, compound

HRID 2179789Notes

Reaction equation

HRID 2179789 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([CH3:49])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:48])[CH2:12][CH2:13][C@@:14]3([C:30]([NH:32][C@@H:33]4[CH2:36][C@H:35]([C:37]([NH:39][CH2:40][CH2:41][C:42]([O:44]C)=[O:43])=[O:38])[C:34]4([CH3:47])[CH3:46])=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:51])[CH3:50])(=O)C>CO.C1COCC1.[OH-].[Na+]>[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([CH3:49])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:48])[CH2:12][CH2:13][C@@:14]3([C:30]([NH:32][C@@H:33]4[CH2:36][C@H:35]([C:37]([NH:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[O:38])[C:34]4([CH3:47])[CH3:46])=[O:31])[CH2:26][CH2:25][C@@H:24]([C:27]([CH3:29])=[CH2:28])[C@@H:15]32)[C:6]1([CH3:51])[CH3:50]

Participants

4

Reactant 1

HCID 50925293HCID 50925293, compound

Product 1

HCID 50923076HCID 50923076, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-((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)propanoate (Example 37, 0.150 g, 0.211 mmol) in MeOH:THF (2:1) (7.5 ml), 2N NaOH (2.5 ml) was added at about 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. 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: 0.030 g: Yield: 21.7%; 1H NMR (300 MHz, DMSO-d6): δ 7.61 (brm, 1H), 7.54 (d, 1H, J=7.2 Hz), 4.63 (s, 1H), 4.52 (s, 1H), 2.90-2.80 (m, 1H), 3.20-3.08 (m, 3H), 3.00-2.89 (m, 3H), 2.68-2.54 (m, 2H), 2.40-2.18 (m, 5H), 1.90-1.74 (m, 2H), 1.70-1.00 (m, 28H), 0.90, 0.86, 0.84, 0.75, 0.72, 0.64 (s, 15H); Mass: [M+1]+ 653 (2%), [M+Na]+ 675 (100%); IR (KBr, cm−1): 3408, 2947, 2868, 1724, 1652, 1636, 1523, 1376, 1250, 1194, 1108, 1074, 1033, 983, 881, 730; M.R: 188.6° C.-200.1° C.; HPLC: 99.35%.

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-dd93c50d92094e5394f715e96dc164e7
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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