1,1'-Carbonyldiimidazole → benzyl (S)-2-((R)-3-((S)-1-(benzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclopentylpropylmethylcarbamate

HRID 1254376노트

반응식

HRID 1254376 반응식
[CH2:1]([O:8][C:9](=[O:21])[N:10]([CH2:12][CH:13]([NH2:20])[CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:27]([N:29]2[CH:33]=N[CH:31]=[CH:30]2)=[O:28])C=1.CCN(C(C)C)C(C)C.[O:43]1[C:47]2[C:48]([C@:52]([C@@H:60]3CCCN[CH2:61]3)([OH:59])[CH2:53][CH2:54][CH2:55][CH2:56][O:57][CH3:58])=[CH:49][CH:50]=[CH:51][C:46]=2[CH:45]=[CH:44]1>C(Cl)Cl>[O:43]1[C:47]2[C:48]([C@:52]([C@@H:60]3[CH2:61][CH2:31][CH2:30][N:29]([C:27]([NH:20][C@@H:13]([CH2:14][CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19]4)[CH2:12][N:10]([CH3:11])[C:9](=[O:21])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:28])[CH2:33]3)([OH:59])[CH2:53][CH2:54][CH2:55][CH2:56][O:57][CH3:58])=[CH:49][CH:50]=[CH:51][C:46]=2[CH:45]=[CH:44]1

참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 59382903(S)-1-(benzofuran-7-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-olHCID 67189318HCID 67189318, 화합물

생성물 1

HCID 57544782benzyl (S)-2-((R)-3-((S)-1-(benzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclopentylpropylmethylcarbamate수율 51.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (2-amino-3-cyclopentyl-propyl)-methyl-carbamic acid benzyl ester (87 mg, 0.3 mmol) and CDI (48.6 mg, 0.3 mmol) in CH2Cl2 (5 mL) cooled to 0-5° C. was added DIEA (0.5 mL). After stirring for 30 minutes, a solution of (S)-1-(benzofuran-7-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (95.1 mg, 0.3 mmol) in CH2Cl2 (3 mL) was added dropwise. The reaction mixture was allowed to warm to rt and stirred overnight. The mixture was washed with water (10 mL). The aqueous layer was extracted with CH2Cl2 (2×15 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by prep HPLC to give benzyl (S)-2-((R)-3-((S)-1-(benzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclopentylpropylmethylcarbamate (98.5 mg, 51.9%).

후처리

  1. stirringstirred overnight
  2. washThe mixture was washed with water (10 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×15 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by prep HPLC

출처 및 근거

ORD 기록
ord-af1c064241c14c639b89ea56adcdfe40
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455521B2

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