Ammonium Chloride → HCID 70234416, 화합물

HRID 850607

반응식

HRID 850607 반응식
[CH2:1]([NH:8][C@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22]([O:26][C:27](=[O:37])[CH:28]=[CH:29][C:30]1[CH:31]=[N:32][C:33]([NH2:36])=[CH:34][CH:35]=1)([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>C1COCC1>[C:22]([O:26][C:27](=[O:37])[CH2:28][C@@H:29]([C:30]1[CH:31]=[N:32][C:33]([NH2:36])=[CH:34][CH:35]=1)[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])([CH3:25])([CH3:23])[CH3:24]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 1268086(+)-BenzylphenethylamineHCID 536654623-(6-Amino-pyridin-3-yl)-acrylic acid tert-butyl esterHCID 178418339Butyllithium

생성물 1

HCID 70234416HCID 70234416, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a cooled (0° C.) solution of (R)-(+)-N-benzyl-α-methylbenzylamine (4.0 g, 19 mmol) in 50 mL THF was gradually added n-butyllithium (11.3 mL, 2.5 M, 28.2 mmol) over 5 min. The mixture was stirred for 30 min at 0° C. and cooled to -78° C. A solution of 9-2 (2.0 g, 9.4 mmol) in 20 mL THF was gradually added. After stirring for 40 min at -78° C., it was treated with NH4Cl (sat.) at -78° C., warmed to room temperature and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After solvent evaporation, the residue was purified using silica gel flash chromatography (EtOAc/hexanes, 1:2) to afford the desired product 9-3 as an oil.

후처리

  1. customover 5 min
  2. temperaturecooled to -78° C
  3. stirringAfter stirring for 40 min at -78° C.
  4. temperaturewarmed to room temperature
  5. extractionextracted three times with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. customAfter solvent evaporation
  9. customthe residue was purified

출처 및 근거

ORD 기록
ord-a3a1a044c4b7454fab5ee1e58e0d02ce
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06017926

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