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

HRID 1988071

반응식

HRID 1988071 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4842c3e460254e08a16f558392042157
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553873B2

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