Diisopropylethylamine → HCID 57657962, 화합물

HRID 391521노트

반응식

HRID 391521 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(CC)C(C)C)(C)C.[CH3:20][S@@:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[NH:23])=[O:22].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:23]=[S@:21]([CH3:20])(=[O:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:9]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 887075-Bromonicotinic acidHCID 2724699PyBOPHCID 25036286(R)-(-)-S-Methyl-S-phenylsulfoximine

생성물 1

HCID 57657962HCID 57657962, 화합물수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-bromonicotinic acid (303 mg, 1.5 mmol), N,N-diisopropylethylamine (0.523 mL, 3.0 mmol), and (R)-(−)-S-methyl-S-phenylsulfoximine (233 mg, 1.5 mmol) in DMF (3.0 mL) cooled to 0° C. was added 1-benzotriazolyloxytripyrrolidinylphosphonium hexafluorophosphate (PyBOP) (859 mg, 1.65 mmol). The solution was stirred 10 minutes, the ice bath removed, and the reaction continued at room temperature for 2.5 hours. The mixture was taken up in EtOAc and washed with H2O, Na2CO3 solution, brine, AcOH solution, H2O, Na2CO3 solution, brine, dried with anhydrous Na2SO4 and rotary evaporated. The brown oil was chromatographed eluting with hexane/EtOAc to give the title compound as a yellow solid (478 mg, 94%).

후처리

  1. customthe ice bath removed
  2. waitthe reaction continued at room temperature for 2.5 hours
  3. washwashed with H2O, Na2CO3 solution, brine, AcOH solution, H2O, Na2CO3 solution, brine
  4. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  5. customThe brown oil was chromatographed
  6. washeluting with hexane/EtOAc

출처 및 근거

ORD 기록
ord-af2c070adbaf49df93bca570f9752336
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383825B2

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