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Hydrochloric Acid → 2-Docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoic acid

HRID 85362
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 85362
[C:1]([NH:24][CH:25]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:26]([O:28]C)=[O:27])(=[O:23])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH3:22].[OH-].[Na+].Cl>CO>[C:1]([NH:24][CH:25]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:26]([OH:28])=[O:27])(=[O:23])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH3:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 72539769Methyl 2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoate

Produkt 1

HCID 725397302-Docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoate (610 mg, 1.34 mmol) in MeOH (15 mL) was added 2M aqueous NaOH (30 mL). The reaction mixture was heated (50° C., 16 h), cooled (RT), and acidified with 2M aqueous HCl to pH 1. The mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, (MeOH:DCM, 0-10%) to afford 2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoic acid (0.51 g, 89%) as a light yellow solid. Mass calculated for C28H43NO3=441.65; found: [M+H]+=442.1.

Aufarbeitung

  1. temperaturecooled (RT)
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography, (MeOH:DCM, 0-10%)

Quellen und Nachweise

ORD-Eintrag
ord-dcbc4deca9284d3cab0d310334fd766b
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846972B2

Notizen zur Reaktion

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