Ethyl Acetate → (R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyril

HRID 1828337

Reaktionsgleichung

Reaktionsgleichung von HRID 1828337
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]1=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].C[O-].[Na+].C(OCC)(=O)C>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:10]1=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 60984Methyl bromoacetateHCID 10942334Sodium MethoxideHCID 69198597(R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril

Produkt 1

HCID 69194872(R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyrilAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(R)-3-t-butyloxycarbonylamino-3,4-dihydrocarbostyril (26 mg), as prepared in Example 5, was dissolved in tetrahydrofuran (5 mL) at room temperature under argon. To the stirring solution was added methyl bromoacetate (31 mg), followed by sodium methoxide (26 mg). The resulting suspension was stirred for 30 min before dilution with ethyl acetate (25 mL) and water (25 mL). The organic phase was separated, washed with water (25 mL), and dried over anhydrous sodium sulfate. After solvent evaporation under vacuum, the crude product was purified by reverse phase preparative HPLC to provide (R)-3-t-butyloxycarbonylamino-1-carbomethoxymethyl-3,4-dihydrocarbostyril (24 mg).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with water (25 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter solvent evaporation under vacuum
  5. customthe crude product was purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-577c729936e1488d86acc2ce35c04ab7
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07057046B2

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