Water → Methyl 3-benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylate

HRID 1453866노트

반응식

HRID 1453866 반응식
[N:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:11]([C:12](OC)=[O:13])=[C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]([C:24]([O:26][CH3:27])=[O:25])=[N:8]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH2:17]([O:16][C:10]1[C:9]([C:24]([O:26][CH3:27])=[O:25])=[N:8][N:7]2[CH2:6][CH2:5][CH2:4][NH:1][C:12](=[O:13])[C:11]=12)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86617824HCID 86617824, 화합물

생성물 1

HCID 68952653Methyl 3-benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of dimethyl 1-(3-azidopropyl)-4-benzyloxy-1H-pyrazole-3,5-dicarboxylate (152 mg, 0.407 mmol) in THF (2 mL) were added triphenylphosphine (107 mg, 0.407 mmol) and water (37 μL, 2.036 mmol). The reaction was stirred at room temperature overnight, and the solvent was removed in vacuo. The residue was dissolved in toluene and heated to 110° C. overnight. Purification by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions afforded the title product. 1H NMR (400 MHz, CDCl3) δ 7.44-7.41 (m, 2H), 7.34-7.28 (m, 3H), 6.70 (br s, 1H), 5.29 (s, 2H), 4.46-4.42 (t, 2H), 3.96 (s, 3H), 3.06-3.00 (m, 2H), 2.20-2.13 (m, 2H); ES MS (M+1)=316.

후처리

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in toluene
  3. temperatureheated to 110° C. overnight
  4. customPurification by reverse phase chromatography on a C-18 column
  5. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions

출처 및 근거

ORD 기록
ord-a9bc9b4c3103489dbe5559f35006fd05
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476666B2

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