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Hydrochloric Acid → HCID 58292863、化合物

HRID 1798285
ノート
印刷プレビュー

反応式

HRID 1798285 の反応式
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[C:25]([O:29][C:30]([C:32]1[S:36][C:35](Cl)=[N:34][CH:33]=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].Cl>CN(C=O)C>[C:25]([O:29][C:30]([C:32]1[S:36][C:35]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:34][CH:33]=1)=[O:31])([CH3:28])([CH3:26])[CH3:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 24229786tert-Butyl 2-chloro-1,3-thiazole-5-carboxylateHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

生成物 1

HCID 58292863HCID 58292863、化合物収率 95.2%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a solution of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (2 g, 8 mmol), Cs2CO3 (7.82 g, 24 mmol) and t-butyl-2-chloro-1,3-thiazole-5-carboxylate (2.64 g, 12 mmol) in DMF (20 mL) was heated at 80° C. for 1 h. The reaction mixture was cooled down and acidified to pH 3 with 6N HCl, extracted with ethyl acetate and washed with water and brine. The organic layer was dried by Na2SO4 and concentrated. The residue was purified by column chromatography (silica, Hexanes/EA=8:2, then DCM/MeOH=9:1) affording the title compound (3.3 g, 89%) as a light yellow solid. 1H NMR (CDCl3) δ 8.01 (s, 1H), 7.46 (d, 1H), 7.18 (d, 1H), 5.68 (dd, 1H), 4.21 (q, 2H), 3.11 (dd, 1H), 2.44 (m, 1H), 2.39 (s, 3H), 1.56 (s, 9H), 1.24 (t, 3H).

後処理

  1. temperatureThe reaction mixture was cooled down
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried by Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica, Hexanes/EA=8:2

出典と根拠

ORDレコード
ord-476dd4c7ee244a4c8a250755c1ab0c56
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08343944B2

反応ノート

読み込み中…

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