N-Allylaniline → HCID 68292774, 화합물

HRID 529475

반응식

HRID 529475 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([CH3:17])([CH3:16])[CH:14]=[CH2:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:19]=[CH2:20].CCN(C(C)C)C(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CCOC(C)=O>[CH2:18]([N:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10](=[O:12])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:13]([CH3:17])([CH3:16])[CH:14]=[CH2:15])[CH:19]=[CH2:20]

참가 물질

6

반응물 4

HCID 68525N-AllylanilineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 113685192-((Tert-butoxycarbonyl)amino)-3,3-dimethylpent-4-enoic acid

생성물 1

HCID 68292774HCID 68292774, 화합물수율 40.6%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

반응 조건

온도
0 °C

실험 절차

To a round bottom flask was added 2-(tert-butoxycarbonylamino)-3,3-dimethylpent-4-enoic acid (120 mg, 0.493 mmol), N-allylaniline (0.134 mL, 0.986 mmol), EtOAc (5 mL) and Hunig's Base (0.258 mL, 1.48 mmol). The reaction mixture was cooled to 0° C. 1-propanephosphonic acid cyclic anhydride (314 mg, 0.986 mmol) was added and the reaction was stirred at 0° C. for 5 min and then at rt for 3 days. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (10 mL) and saturated aqueous NaCl (10 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was purified by RP prep-HPLC (Method A) to give tert-butyl 1-(allyl(phenyl)amino)-3,3-dimethyl-1-oxopent-4-en-2-ylcarbamate (70 mg, 0.20 mmol, 40% yield) as clear oil. Anal. Calcd. for C21H30N2O3 m/z 358.2. found: 359.2 (M+H)+.

후처리

  1. waitat rt for 3 days
  2. washwashed with water (10 mL) and saturated aqueous NaCl (10 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by RP prep-HPLC (Method A)

출처 및 근거

ORD 기록
ord-2fc6b8c39b1f4cf4985b6ae14e871e6b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346852B2

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