Methanesulfonyl chloride → Ethyl 2-(1-hydroxy-4-methyl-6-(methylsulfonyloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798136ノート

反応式

HRID 1798136 の反応式
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.CCN(C(C)C)C(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][S:29]([CH3:28])(=[O:31])=[O:30])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

生成物 1

HCID 58292870Ethyl 2-(1-hydroxy-4-methyl-6-(methylsulfonyloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (500 mg, 2 mmol), DIPEA (774 mg, 6 mmol) in DCM (10 mL) was slowly added MsCl (366 mg, 3.2 mmol) at −78° C. The reaction mixture was stirred overnight at room temperature, quenched with saturated NH4Cl and washed with saturated NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was used directly in next step reaction without further purification. MS (ESI) m/z=329 [M+H]+

後処理

  1. customat −78° C
  2. customquenched with saturated NH4Cl
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was used directly in next step reaction without further purification

出典と根拠

ORDレコード
ord-3d438335609c4777b2fcba36f1361e50
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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