HCID 66858893, compound → HCID 66859993, compound

HRID 2179825Notes

Reaction equation

HRID 2179825 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:14][C@@H:13]([NH:15][C:16]([C@:18]23[CH2:53][CH2:52][C@@H:51]([C:54]([CH3:56])=[CH2:55])[C@@H:19]2[C@@H:20]2[C@@:33]([CH3:36])([CH2:34][CH2:35]3)[C@@:32]3([CH3:37])[C@@H:23]([C@:24]4([CH3:50])[C@@H:29]([CH2:30][CH2:31]3)[C:28]([CH3:39])([CH3:38])[C@@H:27]([O:40][C:41](=[O:49])[CH2:42][C:43]([CH3:48])([CH3:47])[C:44]([OH:46])=[O:45])[CH2:26][CH2:25]4)[CH2:22][CH2:21]2)=[O:17])[C:12]1([CH3:58])[CH3:57])=[O:10])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:44]([C:43]([CH3:48])([CH3:47])[CH2:42][C:41]([O:40][C@H:27]1[CH2:26][CH2:25][C@@:24]2([CH3:50])[C@@H:29]([CH2:30][CH2:31][C@:32]3([CH3:37])[C@@H:23]2[CH2:22][CH2:21][C@H:20]2[C@@:33]3([CH3:36])[CH2:34][CH2:35][C@@:18]3([C:16]([NH:15][C@@H:13]4[CH2:14][C@H:11]([C:9]([OH:10])=[O:8])[C:12]4([CH3:58])[CH3:57])=[O:17])[CH2:53][CH2:52][C@@H:51]([CH:54]([CH3:56])[CH3:55])[C@@H:19]32)[C:28]1([CH3:39])[CH3:38])=[O:49])([OH:46])=[O:45]

Participants

4

Reactant 1

HCID 66858893HCID 66858893, compound

Product 1

HCID 66859993HCID 66859993, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1R,3S)-3-(benzyloxycarbonyl)-2,2-dimethylcyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid (Example 87, 200 mg) in EtOAc (20 ml) at room temperature 10% Pd/C (catalytic amount) were added and the reaction mixture was stirred under H2 gas atmosphere at room temperature for 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was filtered through a celite bed and the obtained filtrate was concentrated under reduced pressure to afford the debenzylated title compound as a white solid. Wt: 0.100 g: Yield: 56.2%. 1H NMR (300 MHz, CDCl3): δ 5.77 (d, J=7.8 Hz, 1H), 4.54-4.507 (m, 1H), 4.157-4.13 (m, 1H), 2.9-2.80 (m, 1H), 2.7-2.61 (m, 3H), 2.60-2.20 (m, 5H), 2.00-1.93 (m, 1H), 1.80-1.10 (m, 30H), 0.95 (s, 6H), 0.941 (s, 3H), 0.88 (s, 6H), 0.84 (d, J=7.6 Hz, 6H), 0.832 (s, 3H), 0.823 (s, 3H); IR (KBr, cm−1): 3403, 2956, 2620, 1710, 1652, 1648, 1509, 1474, 1367, 1245, 1194, 1148, 1000, 978, 877, 620, 509; M.R: 150.1° C.-282.9° C.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. filtrationthe reaction mixture was filtered through a celite bed
  3. concentrationthe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7b49276c8074802806b9bf8ec49426c
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…