1-Hydroxybenzotriazole → HCID 58677920, 화합물

HRID 2102224노트

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HRID 2102224 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.Cl.[CH3:14][NH:15][O:16][CH3:17].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:15]([O:16][CH3:17])[CH3:14])=[O:12])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27356093-(4-Bromophenyl)propionic acid

생성물 1

HCID 58677920HCID 58677920, 화합물

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 24.95 g 3-(4-bromophenyl)propionic acid, 12.75 g N,O-dimethylhydroxylamine hydrochloride, 27.14 g EDC, and 17.66 g HOBt were added 300 mL DMF and 47.4 mL DIEA. The reaction mixture was stirred at room temperature for 17 hours and then poured into 700 mL ice water, extracted with 5×200 mL EtOAc. The combined EtOAc solution was washed with 200 mL 5% NaHCO3, 4×200 mL water, and 200 mL saturated brine, dried over Na2SO4, and concentrated under reduced pressure to give crude product as a yellow oil. It was purified on silica gel using 35-55% EtOAc in hexanes to give the title compound as yellowish oil. 1H NMR (CDCl3, 500 MHz) δ 7.40˜7.43 (m, 2H), 7.11˜7.14 (m, 2H), 3.63 (s, 3), 3.19 (s, 3H), 2.93 (t, J=7.8 Hz, 2H), 2.73 (t, J=7.7 Hz, 2H). LC-MS: 1.77 min. (M+H=272.1/274).

후처리

  1. extractionextracted with 5×200 mL EtOAc
  2. washThe combined EtOAc solution was washed with 200 mL 5% NaHCO3, 4×200 mL water, and 200 mL saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give crude product as a yellow oil
  6. customIt was purified on silica gel using 35-55% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-b10dc7376fa34739b2e31bdb112136a6
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572922B2

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