Boron tribromide → HCID 57725575、化合物

HRID 2370544ノート

反応式

HRID 2370544 の反応式
C[O:2][C:3]1[CH:19]=[CH:18][C:6]2[N:7]=[C:8]([NH:10][C@@H:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]3[OH:17])[S:9][C:5]=2[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:17][C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:8]1[S:9][C:5]2[CH:4]=[C:3]([OH:2])[CH:19]=[CH:18][C:6]=2[N:7]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 57725706HCID 57725706、化合物

生成物 1

HCID 57725575HCID 57725575、化合物収率 115.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To the solution of (1R,2R)-2-(6-methoxybenzo[d]thiazol-2-ylamino)cyclohexanol (1.06 g, 3.81 mmol) in 16 ml of DCM was added 1 M boron tribromide in DCM (8 ml, 8 mmol) slowly at 0° C. The reaction solution was stirred at room temperature for 2 hours. Removal of all solvent in vaccuo, followed by quenching with water (ca. 30 ml) and diluted NaHCO3 solution, and extraction of aqueous phase with ethyl acetate (3×100 ml) and drying of combined organic extracts over Na2SO4 and subsequent removal of ethyl acetate in vaccuo yielded the desired product (1.16 g) as pink solid. The residue was purified by flash column chromatography to give 2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-ol (1.0 g, 3.78 mmol) as brown solid. ES/MS m/z 265.1 (MH+).

後処理

  1. customRemoval of all solvent in vaccuo
  2. customby quenching with water (ca. 30 ml) and diluted NaHCO3 solution, and extraction of aqueous phase with ethyl acetate (3×100 ml)
  3. dry with materialdrying of combined organic extracts over Na2SO4 and subsequent removal of ethyl acetate in vaccuo

出典と根拠

ORDレコード
ord-5b1e5ccd970a44ac90438c4d7bce07e2
出典データセット
uspto-grants-2014_04
特許番号
US08710048B2

反応ノート

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