Hydrochloric Acid → (5Z)-N-ethyl-7-((1R,2R,3R,5S)-5-hydroxy-2-((S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enamide

HRID 517404Notes

Reaction equation

HRID 517404 reaction equation
[C:1]1([CH2:7][CH2:8][C@H:9]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)/[CH:10]=[CH:11]/[C@@H:12]2[C@@H:24]3[C@@H:15]([O:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23]3)[CH2:14][C@H:13]2[O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:40]([NH2:42])[CH3:41].Cl>O1CCCC1.O>[CH2:40]([NH:42][C:17](=[O:25])[CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][C@H:24]1[C@@H:15]([OH:16])[CH2:14][C@@H:13]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C@@H:12]1/[CH:11]=[CH:10]/[C@@H:9]([O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1)[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:41]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 117875096(6Z,8aR,9R,10R,11aS)-4,5,8,8a,9,10,11,11a-octahydro-9-((S,E)-5-phenyl-3-(tetra hydro-2H-pyran-2-yloxy)pent-1-enyl)-10-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]oxecin-2(3H)-one

Product 1

HCID 58700551(5Z)-N-ethyl-7-((1R,2R,3R,5S)-5-hydroxy-2-((S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enamideYield 73.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of (6Z,8aR,9R,10R,11aS)-4,5,8,8a,9,10,11,11a-octahydro-9-((S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-10-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]oxecin-2(3H)-one (3.0 g, 5.57 mmol) in 15 mL tetrahydrofuran (THF) was treated with 2 M ethylamine (31 ml) in THF. This mixture was stirred and heated at 40° C. over 18 hours under an atmosphere of nitrogen. The mixture was diluted with 50 mL water and the pH was adjusted to 6 with 1N HCl. The layers were separated and the aqueous layer was extracted with 20 mL ethyl acetate twice. The organic layer is dried over magnesium sulfate and concentrated under reduced pressure. Then, the crude product was purified by column chromatography providing 2.4 g of the title compound (73.8% yield).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with 20 mL ethyl acetate twice
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThen, the crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b70944a9cf184f2992c3490e93af01f7
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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