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Triethylamine → (3-(3-(2-Hydroxyethyl)benzyl)-7-oxa-3,10-diazaspiro[5.6]dodecan-10-yl)(2-methylthiazol-4-yl)methanone

HRID 1689443
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1689443
FC(F)(F)C(O)=O.[CH3:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([N:16]2[CH2:27][CH2:26][C:20]3([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[O:19][CH2:18][CH2:17]2)=[O:15])[N:13]=1.C(N(CC)CC)C.Br[CH2:36][C:37]1[CH:38]=[C:39]([CH2:43][CH2:44][OH:45])[CH:40]=[CH:41][CH:42]=1>C(#N)C>[OH:45][CH2:44][CH2:43][C:39]1[CH:38]=[C:37]([CH:42]=[CH:41][CH:40]=1)[CH2:36][N:23]1[CH2:24][CH2:25][C:20]2([CH2:26][CH2:27][N:16]([C:14]([C:12]3[N:13]=[C:9]([CH3:8])[S:10][CH:11]=3)=[O:15])[CH2:17][CH2:18][O:19]2)[CH2:21][CH2:22]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 67292347(2-Methylthiazol-4-yl)(7-oxa-3,10-diazaspiro[5.6]dodecan-10-yl)methanone trifluoroacetate

Produkt 1

HCID 57989079(3-(3-(2-Hydroxyethyl)benzyl)-7-oxa-3,10-diazaspiro[5.6]dodecan-10-yl)(2-methylthiazol-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of (2-methylthiazol-4-yl)(7-oxa-3,10-diazaspiro[5.6]dodecan-10-yl)methanone trifluoroacetate (example 89, step g) (0.21 g) in acetonitrile (15 mL) was treated with triethylamine (0.214 mL) followed by 2-(3-(bromomethyl)phenyl)ethanol (example 6, step a) (0.121 g). The reaction mixture was stirred for 3 hours at 20° C. The solvent was evaporated under reduced pressure and the residue was partitioned between DCM and saturated sodium bicarbonate solution. The aqueous layer was re-extracted twice with DCM and the combined organics were dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 6% methanol in dichloromethane with 1% triethylamine as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.21 g.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between DCM and saturated sodium bicarbonate solution
  3. extractionThe aqueous layer was re-extracted twice with DCM
  4. dry with materialthe combined organics were dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by flash silica chromatography
  8. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8dccb872f0c64eb48b82b2ac5d853a3b
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08148373B2

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