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Sodium Methoxide → HCID 178450818, Verbindung

HRID 2169127
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2169127
C(O)(=O)C.[C:5]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([NH2:14])=[NH:13].C[O:22][C:23](=O)/[C:24](/[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[C:25](\O)/[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C[O-].[Na+]>CO>[C:29]([O:28][C:26]([C:25]1[C:24]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:23]([OH:22])[N:14]=[C:12]([CH2:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:13]=1)=[O:27])([CH3:32])([CH3:30])[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10942334Sodium MethoxideHCID 546790054-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarateHCID 867257812-Biphenyl-2-yl-acetamidine acetic acid salt

Produkt 1

HCID 178450818HCID 178450818, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-biphenyl-2-yl-acetamidine acetate salt (5-01) (2.5 g, 9.2 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (4.2 g, 13.88 mmol) in methanol (60 mL) was added sodium methoxide (1.5 g, 27.77 mmol) at 0° C., then the reaction mixture was allowed to warm to room temperature and was stirred for 16 h. After completion of the reaction, it was quenched with 1N HCl, evaporated and w ater was added. The mixture was extracted with ethyl acetate and the separated organic part was dried over sodium sulfate and concentrated under reduced pressure to get a crude product, which was purified using a normal silica column using 30% ethyl acetate in hexane to get 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (6-01) (2.5 g, 57.63%) as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction, it
  2. customwas quenched with 1N HCl
  3. customevaporated
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe separated organic part was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto get a crude product, which
  9. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-f6665b0fd9a14dd2a6d62de2d29aca62
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09045486B2

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