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Sodium Hydroxide → 1-[(Tert-butoxy)carbonyl]-2-methylazetidine-2-carboxylic acid

HRID 408621
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 408621
CC[O:3][C:4]([C:6]1([CH3:17])[CH2:9][CH2:8][N:7]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:5].[OH-].[Na+]>CCO>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:6]1([CH3:17])[C:4]([OH:5])=[O:3])=[O:11])([CH3:16])([CH3:14])[CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 705629701-Tert-butyl 2-ethyl 2-methylazetidine-1,2-dicarboxylate

Produkt 1

HCID 218663321-[(Tert-butoxy)carbonyl]-2-methylazetidine-2-carboxylic acidAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 2-methyl-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (63 g, 1 eq.) in 260 mL of EtOH was added 260 mL of an aqueous solution of NaOH 2N (2 eq.). The reaction was stirred at 20° C. for 15 h. The solvent was removed under reduced pressure and the crude was partitioned between water and EtOAc. The organic layer was discarded and the aqueous layer was acidified by addition of a solution of citric acid 10% in water until pH=5 and thoroughly extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford 2-methyl-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester (50 g, yield=89%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe crude was partitioned between water and EtOAc
  3. additionthe aqueous layer was acidified by addition of a solution of citric acid 10% in water until pH=5
  4. extractionthoroughly extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-04e9acc75f9148b39d0752e0eabcbbd9
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08759334B2

Notizen zur Reaktion

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