Boron tribromide → HCID 57725507、化合物

HRID 2370559ノート

反応式

HRID 2370559 の反応式
[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[OH:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:19]C.B(Br)(Br)Br>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[OH:18])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:19]

参加物

5

反応物 2

HCID 25134Boron tribromideHCID 57725478HCID 57725478、化合物

生成物 1

HCID 57725507HCID 57725507、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To the solution of (1R,2R)-2-(7-bromo-6-methoxybenzo[d]thiazol-2-ylamino) cyclohexanol (191 mg, 0.537 mmol, 1.0 eq) in 10 mL of DCM was added 1 M solution of boron tribromide (ca. 3.0 mL, 2.68 mmol, 5.0 eq) at room temperature. The reaction mixture was refluxed for 12 hours, thereafter the mixture was diluted with saturated sodium bicarbonate (ca. 100 mL) till PH=7 and aqueous layer extracted with ethyl acetate (ca. 150 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure to give sufficiently pure crude product which was carried to next step without further purification LC/MS (m/z) [345.0] (MH+)

後処理

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. extractionextracted with ethyl acetate (ca. 150 mL×3)
  3. dry with materialCombined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customcondensed under reduced pressure
  6. customto give sufficiently pure crude product which
  7. customwas carried to next step without further purification LC/MS (m/z) [345.0] (MH+)

出典と根拠

ORDレコード
ord-30adfab22ea847d59b52708ef8454832
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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