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2-[3-(tert-Butyldimethylsilanyloxy)propyl]thiazole → 7-{2-[3-(tert-Butyldimethylsilanyloxy)propyl]thiazol-5-yl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester 6-methyl ester

HRID 1096874
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1096874
[Li]CCCC.[Si:6]([O:13][CH2:14][CH2:15][CH2:16][C:17]1[S:18][CH:19]=[CH:20][N:21]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH3:22][O:23][C:24]([C:26]1[CH:27]2[N:42]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH:31]([CH2:32][C:33]=1OS(C(F)(F)F)(=O)=O)[CH2:30][N:29]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:28]2)=[O:25]>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][O:23][C:24]([C:26]1[CH:27]2[N:42]([C:43]([O:45][C:46]([CH3:49])([CH3:47])[CH3:48])=[O:44])[CH:31]([CH2:32][C:33]=1[C:19]1[S:18][C:17]([CH2:16][CH2:15][CH2:14][O:13][Si:6]([C:9]([CH3:12])([CH3:10])[CH3:11])([CH3:7])[CH3:8])=[N:21][CH:20]=1)[CH2:30][N:29]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:28]2)=[O:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 225033152-[3-(tert-Butyldimethylsilanyloxy)propyl]thiazoleHCID 866370767-Trifluoromethanesulfonyloxy-3,9-diazabicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester 6-methyl esterHCID 178418339Butyllithium

Produkt 1

HCID 866370777-{2-[3-(tert-Butyldimethylsilanyloxy)propyl]thiazol-5-yl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester 6-methyl ester
Ausbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

BuLi (1.6 M in hexane, 5.7 mL, 9.1 mmol) was added dropwise to a sol. of 2-[3-(tert-butyldimethylsilanyloxy)propyl]thiazole (1.80 g, 6.79 mmol) in THF (15 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1 h, and ZnCl2 (1M in THF, 11.3 mL, 11.3 mmol) was added dropwise at −78° C. The cooling bath was then removed and the reaction stirred for 1 h while warming up to rt. A sol. of compound Y (2.00 g, 3.77 mmol) in THF (5 mL) was added dropwise, followed by Pd(PPh3)4 (126 mg, 0.109 mmol). The reaction mixture was stirred at rt for 2 h, then partitioned between EtOAc and aq. 1M NaOH, and the layers were separated. The aq. layer was extracted with EtOAc. The combined org. layers were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification by FC (heptane/EtOAc= 7/3) yielded the title compound (1.75 g, 73%). LC-MS: tR=1.20 min, ES+: 638.35.

Aufarbeitung

  1. customThe cooling bath was then removed
  2. stirringthe reaction stirred for 1 h
  3. temperaturewhile warming up to rt
  4. stirringThe reaction mixture was stirred at rt for 2 h
  5. custompartitioned between EtOAc and aq. 1M NaOH
  6. customthe layers were separated
  7. extractionThe aq. layer was extracted with EtOAc
  8. washlayers were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customthe solvents were removed under reduced pressure
  12. customPurification by FC (heptane/EtOAc= 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-eca7b4e75d83483dacb66c00ad0b1b61
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138340B2

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