Potassium hydride → N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine

HRID 2209637노트

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HRID 2209637 반응식
[C:1]([NH:20][CH:21]([CH2:40][OH:41])[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[O:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)=[CH:27][CH:26]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[K+].[C:44]1([CH2:50][CH2:51][CH2:52][CH2:53]I)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1COCC1>[C:1]([NH:20][CH:21]([CH2:40][O:41][CH2:53][CH2:52][CH2:51][CH2:50][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:22][O:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[O:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)=[CH:29][CH:30]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 82127Potassium hydrideHCID 12709818(4-Iodobutyl)benzeneHCID 19420787N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine

생성물 1

HCID 19420792N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine (0.4 g; 0.74 mmol) is added to a suspension of potassium hydride (0.12 g; 1. mmol; 35% suspension in oil) in dry THF (4 ml) at 0° C. The reaction is stirred for 15 minutes at 20° C. 4-Phenyl-1-butyl iodide (0.21 g; 0.81 mmol) is added and the reaction mixture stirred for 15 hours. The reaction is quenched with MeOH, diluted with CH2Cl2 and washed with water 2×. The organic phase is dried (Na2SO4), concentrated and purified by column chromatography with 80% CH2Cl2 /20% petroleum ether to yield N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine as an oil which is used directly in Step F.

후처리

  1. stirringthe reaction mixture stirred for 15 hours
  2. customThe reaction is quenched with MeOH
  3. additiondiluted with CH2Cl2
  4. washwashed with water 2×
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by column chromatography with 80% CH2Cl2 /20% petroleum ether

출처 및 근거

ORD 기록
ord-f24954508231420986828345d92a83d9
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455260

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