Hydrochloric Acid → HCID 50924853, compound

HRID 2179820Notes

Reaction equation

C([O:5][C:6](=[O:60])[CH2:7][CH:8]1[O:13]C(C)(C)[O:11][CH:10]([CH2:16][CH2:17][NH:18][C:19]([C@:21]23[CH2:56][CH2:55][C@@H:54]([C:57]([CH3:59])=[CH2:58])[C@@H:22]2[C@@H:23]2[C@@:36]([CH3:39])([CH2:37][CH2:38]3)[C@@:35]3([CH3:40])[C@@H:26]([C@:27]4([CH3:53])[C@@H:32]([CH2:33][CH2:34]3)[C:31]([CH3:42])([CH3:41])[C@@H:30]([O:43][C:44](=[O:52])[CH2:45][C:46]([CH3:51])([CH3:50])[C:47]([OH:49])=[O:48])[CH2:29][CH2:28]4)[CH2:25][CH2:24]2)=[O:20])[CH2:9]1)(C)(C)C.Cl>CO>[C:47]([C:46]([CH3:51])([CH3:50])[CH2:45][C:44]([O:43][C@H:30]1[CH2:29][CH2:28][C@@:27]2([CH3:53])[C@@H:32]([CH2:33][CH2:34][C@:35]3([CH3:40])[C@@H:26]2[CH2:25][CH2:24][C@H:23]2[C@@:36]3([CH3:39])[CH2:37][CH2:38][C@@:21]3([C:19]([NH:18][CH2:17][CH2:16][CH:10]([OH:11])[CH2:9][CH:8]([OH:13])[CH2:7][C:6]([OH:60])=[O:5])=[O:20])[CH2:56][CH2:55][C@@H:54]([C:57]([CH3:59])=[CH2:58])[C@@H:22]32)[C:31]1([CH3:42])[CH3:41])=[O:52])([OH:49])=[O:48]

Participants

Conditions

Temperature: 0 °C

Procedure

4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(2-(6-(carboxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)ethylcarbamoyl)-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 80, 0.3 g) was taken in MeOH (3 ml) and cooled the contents to 0° C. then Aq HCl (0.5 ml) was added and the contents were stirred for 6 hours at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was evaporated under reduced pressure. The residue was taken in water and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% methanol in DCM as eluent to furnish the title compound (0.08 g) as a white solid. 1H NMR (300 MHz, CDCl3): 0.57-0.97 (m, 19H); 1.18-1.21 (m, 8H); 1.25-1.41 (m, 12H); 1.49-1.62 (m, 8H); 1.65-1.82 (m, 10H); 1.85-1.98 (m, 4H); 2.56-2.69 (m, 2H); 2.88-3.06 (m, 3H); 3.29-3.38 (m, 1H); 3.89-3.90 (m, 1H); 4.44-4.47 (m, 1H); 4.56 (s, 1H); 4.71 (s, 1H); Mass: 744 [M+1].

Workup

customAfter completion of the reaction (monitored by TLC)
customthe reaction mixture was evaporated under reduced pressure
extractionextracted with DCM
dry with materialthe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1ff1c434a4b4453ab6fda2aad60e3e3d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067966B2

Reaction notes

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