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

HRID 1988072Notes

Reaction equation

HRID 1988072 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 57728787N-{4-[(Pyrimidin-2-yl)amino]benzoyl}-L-glutamic acidYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0ef46a754e324a02b66a7a1d48f73177
Source dataset
uspto-grants-2009_06
Patent number
US07553873B2

Reaction notes

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