Tetrahydrofuran → HCID 70153172, 화합물

HRID 277777

반응식

HRID 277777 반응식
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH:13]=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[CH3:17][C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH3:31])[CH2:20][NH:19]1.O1CCCC1.C([BH3-])#N.[Na+]>CO.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:19]3[CH2:20][C@@H:21]([CH3:31])[N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:23][C@@H:18]3[CH3:17])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrileHCID 24903576(2R,5S)-2,5-Dimethyl-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 70153172HCID 70153172, 화합물

시약·촉매·용매 3

HCID 11026Titanium isopropoxide촉매HCID 702Ethanol용매HCID 22242641Methanol--water (1/1)용매

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온도
60 °C

실험 절차

To a round bottom flask were added 1-(4-cyanobenzyl)-5-formylimidazole (250.0 mg, 1.2 mmole) along with titanium(IV)isopropoxide (1.0 ml, 3.65 mmol), (trans) 2,5-Dimethyl-4-tertbutyloxycarbonylpiprizine (253.7 mg, 1.2 mmol) (prepared as described in Step 1), and tetrahydrofuran (0.4 ml). The reaction was heated at 60° C. for 1.25 hour. The reaction was cooled and sodiumcyanoborohydride (95.0 mg, 1.5 mmol) was added along with ethanol (0.5 ml) and the reaction was stirred at RT for 18 hours. The reaction was diluted with methanol/water (3 ml/1 ml) and the mixture filtered through celite. The filtrate was then concentrated to an oil, dissolved into methanol and put through a High Pressure Liquid Chromatography column. The desired fractions were collected, concentrated, and lyophilized to give the ditrifluoroacetic acid salt of the title compound.

후처리

  1. temperatureThe reaction was cooled
  2. filtrationthe mixture filtered through celite
  3. concentrationThe filtrate was then concentrated to an oil
  4. dissolutiondissolved into methanol
  5. customThe desired fractions were collected
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-746d9af315ab4fb7a69c9a5a5da08560
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358956B1

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