Hydrochloric Acid → 1-[(Tert-butoxy)carbonyl]-3-(ethoxycarbonyl)azetidine-3-carboxylic acid

HRID 1175125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175125
[CH2:1]([O:3][C:4]([C:6]1([C:17]([O:19]CC)=[O:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5])[CH3:2].[OH-].[Na+].Cl>CCO.O>[CH2:1]([O:3][C:4]([C:6]1([C:17]([OH:19])=[O:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:7]1)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 574158971-tert-Butyl 3,3-diethyl azetidine-1,3,3-tricarboxylate

Produkt 1

HCID 574158841-[(Tert-butoxy)carbonyl]-3-(ethoxycarbonyl)azetidine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Azetidine-1,3,3-tricarboxylic acid 1-tert-butyl ester 3,3-diethyl ester (1.2 g; 0.4 mmol) in EtOH (12 ml) is cooled to 5° C. under stirring and combined with NaOH (60 mg; 0.04 mmol) in water (4 ml). The reaction mixture is left at room temperature for 1 hour, heated to 50° C. for 5 minutes, poured on brine, acidified with 2N HCl and extracted with TBME three times. The reaction mixture is extracted with TBME three times, the organic phases are combined, dried over Na2SO4 and evaporated to dryness, yielding the desired product as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 13.58 (bs, 1H); 4.20 (q, 2H); 4.12 (bs, 4H); 1.39 (s, 9H); 1.21 (t, 3H). MS (m/z) ES+: 274 (30; MH+); 174 (100).

Aufarbeitung

  1. additionpoured on brine
  2. extractionextracted with TBME three times
  3. extractionThe reaction mixture is extracted with TBME three times
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7b7fe557d6e54555857fb8942a1cfaf3
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838674B2

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