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

HRID 132940ノート

反応式

HRID 132940 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0aa5d56f61494765b3b5f00dd2a9b740
出典データセット
uspto-grants-2008_06
特許番号
US07388007B2

反応ノート

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