Methanol → N-{4-[(Pyrimidin-2-yl)amino]benzoyl}-L-glutamic acid

HRID 1672246

Reaktionsgleichung

Reaktionsgleichung von HRID 1672246
C([O:3][C:4](=[O:29])[CH:5]([NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:17][CH:16]=1)[CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])C.CO.[OH-].[Na+]>C1COCC1>[N:23]1[CH:24]=[CH:25][CH:26]=[N:27][C:22]=1[NH:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([NH:13][C@H:5]([C:4]([OH:29])=[O:3])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:28])=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 673342072-[4-(Pyrimidin-2-ylamino)-benzoylamino]-pentanedioic acid diethyl ester

Produkt 1

HCID 57728787N-{4-[(Pyrimidin-2-yl)amino]benzoyl}-L-glutamic acidAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-[4-(pyrimidin-2-ylamino)-benzoylamino]-pentanedioic acid diethyl ester (250 mg, 0.62 mmol) in THF (4 mL) was added to MeOH (4 mL), followed by the addition of 1N NaOH solution (5 mL, 5 mmol, 8 equiv.). The mixture was stirred at room temperature overnight. Reaction was complete as determined by HPLC. Solvents were removed by rotavap and a small amount of water (5 mL) was added to make a homogeneous solution. 1N HCl was added dropwise until the solution reached a pH of 4. The solid precipitate was collected by filtration, washed with EtOAc, and dried in vacuum oven. The product N-[4-(pyrimidin-2-ylamino)benzoyl]-L-glutamic acid (120 mg) was isolated in 45% yield. MS (ESI) m/z 343.

Aufarbeitung

  1. customReaction
  2. customSolvents were removed by rotavap
  3. additiona small amount of water (5 mL) was added
  4. addition1N HCl was added dropwise until the solution
  5. filtrationThe solid precipitate was collected by filtration
  6. washwashed with EtOAc
  7. customdried in vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-ea0b7c8f664d4355b87b4b7b7c73ea63
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998965B2

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