Boron tribromide → HCID 57725507, 화합물

HRID 1922266노트

반응식

HRID 1922266 반응식
[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]

참가 물질

5

반응물 2

HCID 25134Boron tribromideHCID 57725478HCID 57725478, 화합물

생성물 1

HCID 57725507HCID 57725507, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

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+).

후처리

  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+)

출처 및 근거

ORD 기록
ord-221815f8cb094649b8bb331c477cff3a
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173689B2

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