1,4-Dioxane → HCID 60152905, compound

HRID 405075Notes

Reaction equation

HRID 405075 reaction equation
C[O:2][C:3](=[O:45])[CH2:4][NH:5][CH2:6][C@:7]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:38])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]2[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1.O1CCOCC1>>[C:3]([CH2:4][NH:5][CH2:6][C@:7]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:38])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]2[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)([OH:45])=[O:2]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 71598429HCID 71598429, compound

Product 1

HCID 60152905HCID 60152905, compoundYield 36.9%

Conditions

Temperature
70 °C

Procedure

To the solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-methoxy-2-oxoethylamino)methyl)-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]chrysen-9-yl)benzoic acid (50 mg, 0.081 mmol) in dioxane (2 ml) sodium hydroxide (0.162 ml, 0.162 mmol) was added. The resulting mixture was stirred at 70° C. for 2 h. The solvent was evaporated and the residue was purified by prep. HPLC to afford the title compound as a white solid (18 mg, 35%). LCMS: m/e 602.4 (MH+), 2.32 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 7.90 (d, J=8.3 Hz, 2H), 7.20 (d, J=8.3 Hz, 2H), 5.18-5.40 (m, 1H), 4.73 (s, 1H), 4.62 (br. s., 1H), 3.96 (d, J=5.0 Hz, 2H), 2.78-2.94 (m, 1H), 2.37-2.60 (m, 1H), 2.10 (s, 2H), 1.78-1.92 (m, 3H), 1.62-1.78 (m, 6H), 1.38-1.61 (m, 8H), 1.16-1.38 (m, 6H), 1.11-1.16 (m, 4H), 1.07 (s, 3H), 1.01 (s, 3H), 0.95 (s, 3H), 0.93 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-1f8dfefbd3c5424198316fd82aeb1154
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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