Sodium Hydroxide → 2-(1-Tert-butoxycarbonyl-5-oxo-azepan-4-YL)acetic acid

HRID 239161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 239161
[OH-].[Na+].C(OC([C:8]1([CH2:23][C:24]([O:26]CC)=[O:25])[C:14](=[O:15])[CH2:13][CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]1)=O)C>O.C1COCC1>[C:19]([O:18][C:16]([N:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH:8]([CH2:23][C:24]([OH:26])=[O:25])[CH2:9][CH2:10]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 866860534-Ethoxycarbonylmethyl-5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Produkt 1

HCID 834890002-(1-Tert-butoxycarbonyl-5-oxo-azepan-4-YL)acetic acidAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

23.3 g sodium hydroxide in 218 mL water was added to 38 g 4-ethoxycarbonylmethyl-5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester in 155 mL THF. The reaction was stirred over night at RT, THF was removed and the mixture was extracted with dichlormethane. The aqueous part was acidified with 3M HCl to pH 3 at 0° C. The aqueous solution was extracted with dichloromethane, dried over magnesium sulfate, concentrated under reduced pressure to give 18.2 g of the desired product. (M+H)+=272

Aufarbeitung

  1. customTHF was removed
  2. extractionthe mixture was extracted with dichlormethane
  3. customwas acidified with 3M HCl to pH 3 at 0° C
  4. extractionThe aqueous solution was extracted with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0e0c6f6c2aab4b7684b45f69e503a4b2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642774B2

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