Hydrochloric Acid → HCID 67777289, compound

HRID 2405513Notes

Reaction equation

HRID 2405513 reaction equation
[C:1]([O:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][NH:19][C:20]([C@:22]12[CH2:60][CH2:59][C@@H:58]([C:61]([CH3:63])=[CH2:62])[C@@H:23]1[C@@H:24]1[C@@:37]([CH3:40])([CH2:38][CH2:39]2)[C@@:36]2([CH3:41])[C@@H:27]([C@:28]3([CH3:57])[C@@H:33]([CH2:34][CH2:35]2)[C:32]([CH3:43])([CH3:42])[C:31]([C:44]2[CH:49]=[CH:48][C:47]([C:50]([O:52]C(C)(C)C)=[O:51])=[CH:46][CH:45]=2)=[CH:30][CH2:29]3)[CH2:26][CH2:25]1)=[O:21])[CH3:16])(=[O:11])[CH2:2][CH2:3][C:4]([O:6]C(C)(C)C)=[O:5].Cl>O1CCOCC1>[C:4]([CH2:3][CH2:2][C:1]([O:12][CH2:13][CH2:14][N:15]([CH3:16])[CH2:17][CH2:18][NH:19][C:20]([C@:22]12[CH2:60][CH2:59][C@@H:58]([C:61]([CH3:63])=[CH2:62])[C@@H:23]1[C@@H:24]1[C@@:37]([CH3:40])([CH2:38][CH2:39]2)[C@@:36]2([CH3:41])[C@@H:27]([C@:28]3([CH3:57])[C@@H:33]([CH2:34][CH2:35]2)[C:32]([CH3:43])([CH3:42])[C:31]([C:44]2[CH:45]=[CH:46][C:47]([C:50]([OH:52])=[O:51])=[CH:48][CH:49]=2)=[CH:30][CH2:29]3)[CH2:26][CH2:25]1)=[O:21])=[O:11])([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67774931HCID 67774931, compound

Product 1

HCID 67777289HCID 67777289, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-((2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(tert-butoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxamido)ethyl)(methyl)amino)ethyl tert-butyl succinate (40 mg, 0.046 mmol) in dioxane (1 mL) was added 4N HCl (0.115 mL, 0.459 mmol). The reaction mixture was stirred at 20° C. for 3 hours. LCMS indicated the formation of desired product. The reaction mixture was neutralized with 1N NaOH and then filtered. The clear solution was purified by prep HPLC to provide the desired product as colourless oil (7.2 mg, 20%). LCMS: m/e 759.34 (M+H)+, 2.37 min (method 1). 1H NMR (400 MHz, Acetic Acid-d4) δ ppm 7.99 (d, J=8.28 Hz, 2H), 7.26 (d, J=8.53 Hz, 2H), 5.33 (d, J=4.77 Hz, 1H), 4.74 (s, 1H), 4.61 (s, 1H), 4.56-4.44 (m, 2H), 3.90-3.65 (m, 2H), 3.62-3.52 (m, 2H), 3.50-3.38 (m, 2H), 3.19-3.05 (m, 1H), 3.01 (s, 3H), 2.72 (s, 4H), 2.58-2.42 (m, 1H), 2.26-2.11 (m, 2H), 1.69 (s, 3H), 1.96-1.07 (m, 19H), 1.04 (s, 3H), 1.02 (s, 3H), 1.02 (s, 3H), 0.97 (s, 3H), 0.95 (s, 3H).

Sources & evidence

ORD record
ord-4ab918c5d94249b09f6320572db78d0c
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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