Ammonium Chloride → 2-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide

HRID 1962860

Reaktionsgleichung

Reaktionsgleichung von HRID 1962860
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:18][CH3:19])[C:15]([OH:17])=O)=[CH:8][CH:7]=2)#[CH:2].ON1C2N=CC=CC=2N=N1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH2:52][C:53]([CH3:59])([CH2:56][O:57][CH3:58])[CH2:54][OH:55].[NH4+].[Cl-]>CC#N.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:18][CH3:19])[C:15]([NH:52][C:53]([CH2:56][O:57][CH3:58])([CH3:59])[CH2:54][OH:55])=[O:17])=[CH:8][CH:7]=2)#[CH:2]

Komponenten

9

Edukt 5

HCID 25517Ammonium ChlorideHCID 181649HOAtHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 133754152-Amino-3-methoxy-2-methylpropan-1-olHCID 59565474(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid

Produkt 1

HCID 595653712-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamideAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (413 mg), 1-hydroxy-7-azabenzotriazole (HOAT) (267 mg), O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (630 mg), 2-amino-3-methoxy-2-methyl-propan-1-ol (180 mg) and triethylamine (0.75 ml) in dry CH3CN (20 ml) were stirred at ambient temperature overnight. The reaction mixture was diluted with ethyl acetate and poured on sat. aq. NH4Cl. The water phase was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (cyclohexane/ethyl acetate 1:1) to give as a yellowish oil 2-(3-Ethynyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (200 mg) as a mixture of diastereoisomers.

Aufarbeitung

  1. extractionThe water phase was extracted 3 times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (cyclohexane/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ac84d842a74f41018a2c4cb78c4fc1ed
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415272B2

Verknüpfte Notizen

Wird geladen…