Toluene → HCID 68733649、化合物

HRID 387518ノート

反応式

HRID 387518 の反応式
C1(C)C=CC=CC=1.[CH2:8]([C@@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(C(C)C)C(C)C.CO[CH:42]1[N:46]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:45]([CH3:55])([CH3:54])[CH2:44][CH2:43]1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH2:8]([C@@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:30])[C@@H:22]([C@H:42]1[N:46]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:45]([CH3:55])([CH3:54])[CH2:44][CH2:43]1)[C:23]1[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 54374212HCID 54374212、化合物HCID 59564912HCID 59564912、化合物

生成物 1

HCID 68733649HCID 68733649、化合物収率 85.1%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

TiCl4 in toluene (3.52 mL, 3.52 mmol) was added to a solution of (R)-4-benzyl-3-(2-(4-bromophenyl)acetyl)oxazolidin-2-one (1.26 g, 3.35 mmol) in DCM (30 mL) at −78° C. DIEA (0.64 mL, 3.69 mmol) was then added to the cold stirring solution. The reaction was stirred at −78° C. for 15 minutes, followed by the addition of a solution of tert-butyl 5-methoxy-2,2-dimethylpyrrolidine-1-carboxylate (1.00 g, 4.36 mmol, see Example F) in DCM (10 mL). The reaction was then warmed to −10° C. and stirred for 2 hours. The reaction was quenched with a saturated NH4Cl solution (20 mL), and the organic fraction was isolated, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography to give (S)-tert-butyl 5-((R)-2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(4-bromophenyl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate (1.63 g, 85%) as a solid.

後処理

  1. temperatureThe reaction was then warmed to −10° C.
  2. stirringstirred for 2 hours
  3. customThe reaction was quenched with a saturated NH4Cl solution (20 mL)
  4. customthe organic fraction was isolated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography

出典と根拠

ORDレコード
ord-cf3cf9d6a3d94336816484f8a32dce5a
出典データセット
uspto-grants-2013_02
特許番号
US08372842B2

反応ノート

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