Bromide ion → (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4R)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one

HRID 132940노트

반응식

HRID 132940 반응식
C(OC(N1C[C@H](O)C[C@@H]1C(O)=O)=O)(C)(C)C.[F:17][C:18]1[CH:19]=[C:20]([CH:50]=[C:51]([F:53])[CH:52]=1)[CH2:21][C@H:22]1[C@@H:26]([C@H:27]2[CH2:31][C@@H:30]([O:32]CC=C)[CH2:29][N:28]2[CH:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:25][C:24](=[O:49])[NH:23]1.FC1C=C(C=C(F)C=1)C[C@H]1[C@@H]([C@H]2C[C@@H](OCC=C)CN2)OC(=O)N1.[Br-].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:53][C:51]1[CH:50]=[C:20]([CH:19]=[C:18]([F:17])[CH:52]=1)[CH2:21][C@H:22]1[C@@H:26]([C@H:27]2[CH2:31][C@@H:30]([OH:32])[CH2:29][N:28]2[CH:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:25][C:24](=[O:49])[NH:23]1

참가 물질

7

반응물 5

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 688616N-Boc-cis-4-hydroxy-D-prolineHCID 67316078(4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4R)-4-(allyloxy)-1-benzhydrylpyrrolidin-2-yl)oxazolidin-2-oneHCID 67316146(4S,5R)-4-(3,5-difluorobenzyl)-5-((2R,4R)-4-(allyloxy)pyrrolidin-2-yl)oxazolidin-2-one

생성물 1

HCID 58608196(4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4R)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one수율 87%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Step J (1): (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4R)-4-(allyloxy)-1-benzhydrylpyrrolidin-2-yl)oxazolidin-2-one. A mixture of (4S,5R)-4-(3,5-difluorobenzyl)-5-((2R,4R)-4-(allyloxy)pyrrolidin-2-yl)oxazolidin-2-one (Step C (8), 2.03 g, 6.0 mmol), benzylhydryl bromide (2.22 g, 9.0 mmol), and potassium carbonate (1.24 g, 9.0 mmol) in acetonitrile (40 mL) was stirred at reflux for 35 min. After cooling to rt, the mixture was filtered and concentrated in vacuo. The crude mixture was purified by Flash Chromatography (silica gel, 0-7.5% methanol/chloroform) to give a slightly yellow oil as the title compound (2.64 g, 87% yield): 1H NMR (CDCl3, 300 MHz) δ 1.95-2.23 (2H, m), 2.36 (1H, t, J=12 Hz), 2.70 (1H, m), 3.02 (2H, d, J=6 Hz), 3.48 (1H, m), 3.71-3.99 (4H, m), 4.70 (1H, s), 4.78 (1H, t, J=6 Hz), 4.93 (1H, s), 5.12 (1H, m), 5.22 (1H, dd, J=3, 18 Hz), 5.84 (1H, m), 6.49 (1H, d, J=6 Hz), 6.67 (1H, m), 7.20-7.39 (11H, m).

후처리

  1. temperatureat reflux for 35 min
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude mixture was purified by Flash Chromatography (silica gel, 0-7.5% methanol/chloroform)

출처 및 근거

ORD 기록
ord-0aa5d56f61494765b3b5f00dd2a9b740
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388007B2

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