Sodium Hydroxide → HCID 67333043, Verbindung

HRID 1672253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672253
C[O:2][C:3](=[O:24])[CH2:4][CH2:5][CH:6]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:11])[CH2:7][OH:8].[OH-].[Na+]>C1COCC1.CO>[C:15]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:14]=[CH:13][C:12]([C:10]([NH:9][CH:6]([CH2:7][OH:8])[CH2:5][CH2:4][C:3]([OH:24])=[O:2])=[O:11])=[CH:17][CH:16]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 67332127HCID 67332127, Verbindung

Produkt 1

HCID 67333043HCID 67333043, VerbindungAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-[(Biphenyl-4-carbonyl)-amino]-5-hydroxy-pentanoic acid methyl ester (333 mg, 1.06 mmol) in THF (10 mL) and MeOH (1.27 mL) was added to 1N NaOH (1.27 mL, 1.27 mmol, 1.2 equiv) at room temperature. The mixture was stirred for 2 hours and TLC indicated the reaction was complete. Solvent was removed and the residue was dissolved in water. After adjusting the pH to 4 with 1N HCl, solid precipitated from the solution. The solid was then collected by filtration, washed with water, and dried under vacuum overnight to afford 240 mg of 4-[(Biphenyl-4-carbonyl)-amino]-5-hydroxy-pentanoic acid in 76.7% yield. MS (ESI) m/z 314.

Aufarbeitung

  1. customSolvent was removed
  2. dissolutionthe residue was dissolved in water
  3. customprecipitated from the solution
  4. filtrationThe solid was then collected by filtration
  5. washwashed with water
  6. customdried under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-93c76c5813e94c0b892d92083c709f73
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998965B2

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