Diisopropylethylamine → Benzamide

HRID 1621180

반응식

HRID 1621180 반응식
F[C:2]1[C:14](F)=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6]CC(O)=O)=[O:5].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC(C)C[C@@H](B1O[C@@H]2C[C@@H]3C[C@H]([C@]2(C)O1)C3(C)C)N.FC(F)(F)C([O-])=O.CCN(C(C)C)C(C)C>CN(C)C=O>[C:4]([NH2:6])(=[O:5])[C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:2]=1

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 44244714(R)-3-Methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butan-1-amineHCID 59816243[(2,3-Difluorobenzoyl)amino]acetic acid

생성물 1

HCID 2331Benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of [(2,3-difluorobenzoyl)amino]acetic acid (0.205 g, 0.95 mmol) in dimethylformamide (10 mL) were added TBTU (0.337 g, 1.0 mmol) and (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butan-1-amine as its trifluoroacetate salt (0.362 g, 0.95 mmol). The mixture was allowed to cool to 0° C. and DIEA (0.498 mL, 2.9 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water (100 mL) and the product partitioned into DCM. The organic layer was dried over sodium sulfate and the solvent removed to give 2,3-difluoro-N-[2-({1R)-3-methyl-1-[(3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide.

후처리

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with water (100 mL)
  3. customthe product partitioned into DCM
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent removed

출처 및 근거

ORD 기록
ord-474a7b3a6cae4cc7a2fc1d8e651e0575
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772536B2

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