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

HRID 1672246

反応式

HRID 1672246 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ea0b7c8f664d4355b87b4b7b7c73ea63
出典データセット
uspto-grants-2011_08
特許番号
US07998965B2

関連ノート

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