Diethyl N-(4-aminobenzoyl)-L-glutamate → 2-[4-(Pyrimidin-2-ylamino)-benzoylamino]-pentanedioic acid diethyl ester

HRID 1672245

反応式

HRID 1672245 の反応式
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([O:10][C:11](=[O:30])[C@H:12]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)[CH3:9]>CN(C=O)C>[CH2:8]([O:10][C:11](=[O:30])[CH:12]([NH:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:17][CH:16]=1)[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH3:9]

参加物

4

反応物 2

HCID 73002Diethyl N-(4-aminobenzoyl)-L-glutamateHCID 744042-Chloropyrimidine

生成物 1

HCID 673342072-[4-(Pyrimidin-2-ylamino)-benzoylamino]-pentanedioic acid diethyl ester収率 69.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

2-Chloropyrimidine (0.72 g, 6.3 mmol) and N-(4-aminobenzoyl)-L-glutamic acid diethyl ester (2.04 g, 6.3 mmol, 1 equiv.) were dissolved in DMF (4 mL) and the resulting mixture was heated to 110° C. for 3 hrs. Reaction was complete as determined by TLC. The mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, and concentrated by rotavap. The residue was purified by column chromatography (silica gel, 50% EtOAc/hexane) to afford 1.75 g of desired product 2-[4-(pyrimidin-2-ylamino)-benzoylamino]-pentanedioic acid diethyl ester in 69% yield. MS (ESI) m/z 399.

後処理

  1. customReaction
  2. temperatureThe mixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated by rotavap
  7. customThe residue was purified by column chromatography (silica gel, 50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-a3f651a449a84e309ce94b47b31d67f3
出典データセット
uspto-grants-2011_08
特許番号
US07998965B2

関連ノート

読み込み中…