Potassium Hydroxide → (1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

HRID 1527431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527431
C([O:3][C:4]([C@@H:6]1[CH2:11][C@:10]2([CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[C@@H:8]([CH2:9]2)[N:7]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:5])C.[OH-].[K+]>CO.C1COCC1.O.CCOC(C)=O>[C:23]([O:22][C:20]([N:7]1[C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][C@:10]2([CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[C@H:8]1[CH2:9]2)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Komponenten

7

Edukt 2

HCID 14797Potassium HydroxideHCID 68284099(1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

Produkt 1

HCID 68284002(1R,3S,5S)-5-(Tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (1R,3S,5S)-5-(tetrahydro-pyran-2-yloxymethyl)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (510 mg, 1.38 mmol) in MeOH (2.3 mL), THF (2.3 mL) and water (2.3 mL) was added KOH (155 mg, 2.76 mmol). The reaction was stirred at 60° C. for 45 min. Then allowed to cool to RT and diluted with EtOAc. The layers were separated, the aqueous layer was acidified by addition of HCl (0.1N, until pH 1) and extracted with EtOAc (×2). The organics were dried (Na2SO4), filtered and concentrated. MS (UPLC/MS): 359.4 [M+NH4]+, 340.4 [M−H]−, 386.4 [M+HCOO]−, 681.5 [2M−H]−; tR (HPLC conditions f): 1.84 min.

Aufarbeitung

  1. temperatureto cool to RT
  2. customThe layers were separated
  3. additionthe aqueous layer was acidified by addition of HCl (0.1N, until pH 1)
  4. extractionextracted with EtOAc (×2)
  5. dry with materialThe organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom1.84 min.

Quellen und Nachweise

ORD-Eintrag
ord-b689de084e9f43d89c3a1d1a7247940a
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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