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Sodium Hydroxide → 7-[2-(2-Hydroxyethoxymethyl)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]-non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester

HRID 1096844
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1096844
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]2[N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:13]([CH2:14][C:15]=1[C:16]1[S:20][C:19]([CH2:21][O:22][CH2:23][CH2:24][OH:25])=[N:18][CH:17]=1)[CH2:12][N:11]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:10]2)=[O:7])C>CCO>[C:37]([O:36][C:34]([N:11]1[CH2:10][CH:9]2[N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:13]([CH2:14][C:15]([C:16]3[S:20][C:19]([CH2:21][O:22][CH2:23][CH2:24][OH:25])=[N:18][CH:17]=3)=[C:8]2[C:6]([OH:7])=[O:5])[CH2:12]1)=[O:35])([CH3:38])([CH3:39])[CH3:40]
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Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 866370647-[2-(2-Hydroxyethoxymethyl)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]-non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester 6-ethyl ester

Produkt 1

HCID 866370687-[2-(2-Hydroxyethoxymethyl)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]-non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Aq. 1M NaOH (1.0 mL) was added to a sol. of the compound C5 (50 mg, 0.090 mmol) in EtOH (1.0 mL). The resulting mixture was stirred at 70° C. for 1 h, cooled to rt and the solvent removed in vacuo. The crude mixture was partitioned between Et2O and aq. sat. NH4Cl. The aq. layer was extracted once more with Et2O, then acidified to pH= 4-5, and extracted again with Et2O. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to yield the title compound (26.4 mg, 56%), which was not further purified. LC-MS: tR=0.82 min, ES+: 526.41.

Aufarbeitung

  1. temperaturecooled to rt
  2. customthe solvent removed in vacuo
  3. customThe crude mixture was partitioned between Et2O and aq. sat. NH4Cl
  4. extractionThe aq. layer was extracted once more with Et2O
  5. extractionextracted again with Et2O
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ce56f1d0d28a4e2b96df3c93fecf2d8c
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138340B2

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