Sodium Methoxide → HCID 178450811, Verbindung

HRID 2169359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169359
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][C:14]([NH2:16])=[NH:15])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.C1(C2(CC(N)=N)CCCC2)C=CC=CC=1.[C:33]([O:37][C:38](=[O:53])/[C:39](/O)=[C:40](\[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)/[C:41](O)=[O:42])([CH3:36])([CH3:35])[CH3:34].C[O-].[Na+]>CO.C(OCC)(=O)C.CCCCCC>[C:33]([O:37][C:38]([C:39]1[C:40]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[C:41]([OH:42])[N:16]=[C:14]([CH2:13][C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:15]=1)=[O:53])([CH3:36])([CH3:34])[CH3:35]

Komponenten

8

Edukt 4

HCID 10942334Sodium MethoxideHCID 867258072-(1-Phenyl-cyclopentyl)-acetamidine HCl saltHCID 867258102-[1-(4-Chlorophenyl)-cyclopentyl]-acetamidineHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester

Produkt 1

HCID 178450811HCID 178450811, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 2-[1-(4-chlorophenyl)-cyclopentyl]-acetamidine; hydrochloride (322) (3.1 g, 11.34 mmol) in methanol (25 mL) was added (E,Z)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (4.19 g, 13.61 mmol) and cooled to 0° C. To this reaction mixture was then added sodium methoxide (25% in methanol) (7.4 mL, 34.03 mmol) and stirred at room temperature for 16 h (TLC; ethyl acetate:hexane=1:1, Rf=0.5). The reaction mixture was diluted with ethyl acetate (300 mL), washed with water (60 mL) and brine (60 mL) and dried and concentrated in vacuo to get crude mass which was purified by CombiFlash eluted with gradient polarity mobile phase (hexane to 50% ethyl acetate in hexane) to get pure 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (323) (5.1 g, 91%) as a light brown solid.

Aufarbeitung

  1. washwashed with water (60 mL) and brine (60 mL)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customto get crude mass which
  5. customwas purified by CombiFlash
  6. washeluted with gradient polarity mobile phase (hexane to 50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-484d261894284809ab340e823713ac9f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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