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Toluene → (2S,4S)-4-Benzyloxycarbonylamino-1-{pentyl-[2'-(1-trityl-1H-tetrazol-5-yl) biphenyl-4-ylmethyl]carbamoyl}pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 425131
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HRID 425131 반응식
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][NH:6]1)=[O:4].[CH2:21]([N:26]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:43]2[N:44]=[N:45][N:46](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:47]=2)=[CH:33][CH:32]=1)[C:27](Cl)=[O:28])[CH2:22][CH2:23][CH2:24][CH3:25].CCN([CH:73]([CH3:75])[CH3:74])C(C)C.[C:76]1([CH3:82])[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][N:6]1[C:27](=[O:28])[N:26]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:43]2[N:47]([C:82]([C:74]3[CH:73]=[CH:75][CH:9]=[CH:5][CH:3]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)[N:46]=[N:45][N:44]=2)=[CH:33][CH:32]=1)=[O:4]
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참가 물질

5

반응물 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 45072528(2S,4S)-4-Benzyloxycarbonylaminopyrrolidine-2-carboxylic Acid Methyl EsterHCID 59556775N-Pentyl-N-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]carbamoyl Chloride

생성물 1

HCID 57648853
(2S,4S)-4-Benzyloxycarbonylamino-1-{pentyl-[2'-(1-trityl-1H-tetrazol-5-yl) biphenyl-4-ylmethyl]carbamoyl}pyrrolidine-2-carboxylic Acid Methyl Ester

반응 조건

온도
90 °C

실험 절차

(2S,4S)-4-Benzyloxycarbonylaminopyrrolidine-2-carboxylic acid methyl ester (1.4 g, 5.1 mmol) and N-pentyl-N-[2′-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]carbamoyl chloride (1 equiv) were dissolved in toluene (100 mL). DIPEA (3 equiv) was added, and the solution was stirred at 90° C. for 16 hours. The solution was cooled, washed with water (100 mL), 1M HCl (100 mL) and saturated aqueous NaHCO3 (100 mL), then dried over Na2SO4. The solvent was evaporated to afford the title compound (3.93 g, 4.5 mmol).

후처리

  1. temperatureThe solution was cooled
  2. washwashed with water (100 mL), 1M HCl (100 mL) and saturated aqueous NaHCO3 (100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-7045059b32aa4444940cb29a20691b2f
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08106082B2

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