Trimethylamine → 3-{2-[2-hydroxy-1-(3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy]acetoxy}propionic acid

HRID 1053551

Reaktionsgleichung

Reaktionsgleichung von HRID 1053551
[OH:1][CH:2]1[CH:19]([CH2:20][CH2:21][CH:22]([O:28]C2CCCCO2)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:5]2[CH2:6][C:7]3[C:12]([CH2:13][CH:4]2[CH2:3]1)=[C:11]([O:14][CH2:15][C:16]([OH:18])=[O:17])[CH:10]=[CH:9][CH:8]=3.O[CH2:36][CH2:37][C:38]([O:40]CC1C=CC=CC=1)=[O:39].CN(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl.CC(OC)(C)C>[OH:1][CH:2]1[CH:19]([CH2:20][CH2:21][CH:22]([OH:28])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:5]2[CH2:6][C:7]3[C:12]([CH2:13][CH:4]2[CH2:3]1)=[C:11]([O:14][CH2:15][C:16]([O:18][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:17])[CH:10]=[CH:9][CH:8]=3

Komponenten

7

Edukt 4

HCID 1146TrimethylamineHCID 84459Propanoic acid, 3-hydroxy-, phenylmethyl esterHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 90281645HCID 90281645, Verbindung

Produkt 1

HCID 1214807453-{2-[2-hydroxy-1-(3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy]acetoxy}propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a solution of Compound B (120 mg, 0.25 mmol), benzyl 3-hydroxypropionate (54 mg, 0.30 mmol) and trimethylamine (140 μL, 1.0 mmol) in DCM (4 mL) was added BOP—Cl (95 mg, 0.38 mmol). The reaction mixture was stirred at RT for 16 hr under nitrogen, diluted with MTBE, washed with brine, dried over sodium sulfate, and concentrated to an oil that was purified by silica gel chromatography. A solution of the THP-protected diester in ethanol (4 mL) was treated with PPTS (50 mg), stirred at 50° C. for 4 hr, and concentrated to an oil that was purified by silica gel chromatography. A solution of the THP-deprotected diester in dioxane (5 mL) was treated with wet 5% Pd/C (20 mg) and stirred for 24 hr under a balloon of hydrogen. The reaction mixture was filtered and concentrated to give crude Compound II-4. MS: m/z 485 [M+Na]+

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to an oil that
  4. customwas purified by silica gel chromatography
  5. additionA solution of the THP-protected diester in ethanol (4 mL) was treated with PPTS (50 mg)
  6. stirringstirred at 50° C. for 4 hr
  7. concentrationconcentrated to an oil that
  8. customwas purified by silica gel chromatography
  9. additionA solution of the THP-deprotected diester in dioxane (5 mL) was treated with wet 5% Pd/C (20 mg)
  10. stirringstirred for 24 hr under a balloon of hydrogen
  11. filtrationThe reaction mixture was filtered
  12. concentrationconcentrated
  13. customto give crude Compound II-4

Quellen und Nachweise

ORD-Eintrag
ord-99aa46029a874eeaa0d37620c04c9656
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394227B1

Verknüpfte Notizen

Wird geladen…