1,8-Diazabicyclo(5.4.0)undec-7-ene → (S)-2-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]propionic acid methyl ester

HRID 348440

Reaktionsgleichung

Reaktionsgleichung von HRID 348440
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14](S(C)=O)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[C:20]([O:25][CH3:26])(=[O:24])[C@@H:21]([CH3:23])[OH:22].C1CCN2C(=NCCC2)CC1>C1COCC1>[CH3:26][O:25][C:20](=[O:24])[C@@H:21]([O:22][C:14]1[N:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:16][N:15]=1)[CH3:23]

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 637514(+)-Methyl lactateHCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Produkt 1

HCID 69523285(S)-2-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]propionic acid methyl esterAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (40 mg, 0.14 mmol) in THF (1 mL) was added (R)-(+)-methyl lactate (20 μL, 0.21 mmol) followed by DBU (34 μL, 0.23 mmol). The solution was stirred for 2 days, quenched with 3% HCl and extracted with ethyl acetate. The organic layers were combined, washed successively with 5% NaHCO3, water, and brine, dried and concentrated in vacuo to afford 19.9 mg (46% yield) of the titled compound as a white solid shown to be 94% pure by HPLC. ESI-MS m/z 320 (MH+), 318 (M−H)−.

Aufarbeitung

  1. customquenched with 3% HCl
  2. extractionextracted with ethyl acetate
  3. washwashed successively with 5% NaHCO3, water, and brine
  4. customdried
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4bfd844e54c04b44934207240dd3e5aa
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176310B1

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