Lithium hydroxide, monohydrate → 1-(Biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid

HRID 1665669

Reaktionsgleichung

Reaktionsgleichung von HRID 1665669
O[Li].O.C[O:5][C:6]([C:8]1([C:11](=[O:25])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:10][CH2:9]1)=[O:7]>CO.C1COCC1.O>[C:16]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[CH:18][C:13]([NH:12][C:11]([C:8]2([C:6]([OH:7])=[O:5])[CH2:10][CH2:9]2)=[O:25])=[CH:14][CH:15]=1

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 578758101-(Biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid methyl ester

Produkt 1

HCID 578743681-(Biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acidAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LiOH.H2O (21 mg, 0.5 mmol) was added to a solution of 1-(biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid methyl ester (100 mg, 0.33 mmol) in methanol (0.5 mL), THF (1 mL) and H2O (0.3 mL) and the resulting mixture was stirred for 2 hours at ambient temperature. The reaction mixture was then concentrated and the residue was diluted with water, acidified with conc. HCl. The resulting precipitate was isolated by filtration and dried to afford 55 mg (58%) of 1-(biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. additionthe residue was diluted with water
  3. customThe resulting precipitate was isolated by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-daf082de2add4ae18fb5243b49170445
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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