Water → HCID 178472378、化合物

HRID 928119ノート

反応式

HRID 928119 の反応式
[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH2:8])=[N:4][CH:3]=1.C[N+]1([O-])CC[O:24]CC1.C1COCC1.[OH2:33]>S([O-])([O-])(=O)=S.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)([OH:24])[CH2:8][OH:33])=[N:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 178437588HCID 178437588、化合物

生成物 1

HCID 178472378HCID 178472378、化合物

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 24477Sodium Thiosulfate溶媒

実験手順

Ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]cyclohexanecarboxylate (40 mg, 0.12 mmol), 4-methylmorpholine N-oxide (31 mg, 0.27 mmol), THF (0.8 ml), water (0.4 ml) and osmium tetroxide (0.22 ml, 0.028 mmol) were combined and the mixture was stirred at room temperature for 40 min. The mixture was then diluted with saturated sodium thiosulfate and extracted with EtOAc. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified on silica gel (EtOAc/hexane=1/1) to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1,2-dihydroxyethyl]cyclohexane-carboxylate. MS ESI calc'd. for C14H20BrNO4S [M+H]+ 378, 380. found 378, 380. 1H NMR (500 MHz, CDCl3) δ 7.55 (s, 1H), 4.15 (dd, J=5.7, 11.1, 1H), 4.07 (q, J=7.1, 2H), 3.74 (dd, J=7.0, 11.1, 1H), 2.61 (t, J=6.4, 1H), 2.20-2.10 (m, 1H), 2.05-1.84 (m, 3H), 1.85-1.70 (m, 1H), 1.60 (d, J=12.8, 1H), 1.46-1.13 (m, 5H), 1.13-1.05 (m, 1H).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel (EtOAc/hexane=1/1)

出典と根拠

ORDレコード
ord-a13af991b984464b872839fe04b2b7ff
出典データセット
uspto-grants-2016_03
特許番号
US09290490B2

反応ノート

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