Boron tribromide → HCID 57725575, 화합물

HRID 1988454노트

반응식

HRID 1988454 반응식
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

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 57725706HCID 57725706, 화합물

생성물 1

HCID 57725575HCID 57725575, 화합물수율 115.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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 vacuo, 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+).

후처리

  1. customRemoval of all solvent in vacuo
  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

출처 및 근거

ORD 기록
ord-3b35e360ecfc4d8b898437f0121b9d86
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553854B2

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