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Hydrochloric Acid → HCID 58292863, 화합물

HRID 1798285
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HRID 1798285 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 1

HCID 58292863HCID 58292863, 화합물수율 95.2%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-476dd4c7ee244a4c8a250755c1ab0c56
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08343944B2

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