Potassium Carbonate → HCID 145834454, compound

HRID 405099Notes

Reaction equation

HRID 405099 reaction equation
[CH:1]([C@:3]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:4]1[C@@H:5]1[C@@:18]([CH3:21])([CH2:19][CH2:20]2)[C@@:17]2([CH3:22])[C@@H:8]([C@:9]3([CH3:38])[C@@H:14]([CH2:15][CH2:16]2)[C:13]([CH3:24])([CH3:23])[C:12]([C:25]2[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:27][CH:26]=2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1)=O.Cl.[NH2:46][OH:47].C(=O)([O-])[O-].[K+].[K+]>CCO>[OH:47]/[N:46]=[CH:1]/[C@:3]12[CH2:41][CH2:40][C@@H:39]([C:42]([CH3:44])=[CH2:43])[C@@H:4]1[C@@H:5]1[C@@:18]([CH3:21])([CH2:19][CH2:20]2)[C@@:17]2([CH3:22])[C@@H:8]([C@:9]3([CH3:38])[C@@H:14]([CH2:15][CH2:16]2)[C:13]([CH3:23])([CH3:24])[C:12]([C:25]2[CH:37]=[CH:36][C:28]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])=[CH:27][CH:26]=2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86676397tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-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)benzoate

Product 1

HCID 145834454HCID 145834454, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-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)benzoate (200 mg, 0.334 mmol) in EtOH (20 mL) was added hydroxylamine hydrochloride (186 mg, 2.67 mmol) and potassium carbonate (369 mg, 2.67 mmol) and the mixture was stirred overnight at room temperature. LC/MS showed the mass of the expected product. The mixture was diluted with 7 mL of sat. NaHCO3 and was extracted with dichloromethane (3×7 mL). The combined organic layers were dried with Na2SO4. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product as an off white foam (˜100%) was used in the next step with no additional purification. LCMS: m/e 614.53 (MH+), 3.82 min (method 3). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.90 (2H, m, J=8.3 Hz), 7.60 (1H, s), 7.19 (2H, m, J=8.3 Hz), 5.23-5.35 (1H, m), 4.76 (1H, d, J=1.8 Hz), 4.64 (1H, s), 2.56 (1H, td, J=11.0, 5.4 Hz), 2.05-2.19 (1H, m), 1.92-2.05 (2H, m), 1.83-1.92 (2H, m), 1.64-1.82 (7H, m), 1.58-1.64 (9H, m), 1.38-1.57 (9H, m), 1.22-1.31 (2H, m), 1.10-1.20 (2H, m), 1.07 (3H, s), 1.04 (3H, s), 0.97-1.01 (3H, m), 0.85-0.97 (6H, m)

Sources & evidence

ORD record
ord-53361e2168f24abfa1d3da993bfb93b2
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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