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Hydrogen Peroxide → 2-Cyclopentylmethyl-3-[formyl-(tetrahydro-pyran-2-yloxy)-amino]-propionic acid

HRID 1666945
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1666945
C(C1COC(=O)N1[C:14](=[O:33])[CH:15]([CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[CH2:16][N:17]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[CH:18]=[O:19])C1C=CC=CC=1.C1C[O:37]CC1.O.OO>[Cl-].[Na+].O>[CH:28]1([CH2:27][CH:15]([CH2:16][N:17]([CH:18]=[O:19])[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:14]([OH:33])=[O:37])[CH2:29][CH2:30][CH2:31][CH2:32]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 8028TetrahydrofuranHCID 76652336HCID 76652336, Verbindung

Produkt 1

HCID 766523532-Cyclopentylmethyl-3-[formyl-(tetrahydro-pyran-2-yloxy)-amino]-propionic acidAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360
Sodium chloride; water
Lösungsmittel

Versuchsvorschrift

N-[3-(4-Benzyl-2-oxo-oxazolidin-3-yl)-2-cyclopentylmethyl-3-oxo-propyl]-N-(tetrahydro-pyran-2-yloxy)-formamide (3.65 g, 7.96 mmol), THF (125 mL), and water (40 mL) is cooled to 4° C. To this mixture, is added 30% H2O2 (5.2 mL, 50.90 mmole) and LiOH monohydrate (0.40 g, 9.53 mmol), respectively. The reaction mixture is stirred for 1.5 hours. The mixture is slowly quenched with 0.5 M Na2SO3, while maintaining the temperature below 15° C. with an ice bath. The quenched mixture is stirred for an addition 30 minutes, concentrated in vacuo until the THF solvent is removed, and washed with EtOAc. The basic reaction mixture is acidified with Amberlite IR-120 resin (H+) to pH=4.5. Brine is added to the acidic solution, and the combined mixture is extracted with EtOAc. The organic layers from the acidic solution washing are combined, dried over Na2SO4, and concentrated in vacuo. This gave 2-cyclopentylmethyl-3-[formyl-(tetrahydro-pyran-2-yloxy)-amino]-propionic acid (1.20 g, 50% yield) as an oil.

Aufarbeitung

  1. customThe mixture is slowly quenched with 0.5 M Na2SO3
  2. temperaturewhile maintaining the temperature below 15° C. with an ice bath
  3. stirringThe quenched mixture is stirred for an addition 30 minutes
  4. concentrationconcentrated in vacuo until the THF solvent
  5. customis removed
  6. washwashed with EtOAc
  7. customThe basic reaction mixture
  8. extractionthe combined mixture is extracted with EtOAc
  9. washThe organic layers from the acidic solution washing
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9d479f233d234e30afb754b6953a8c0a
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08044199B2

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