Diisopropylethylamine → Benzamide

HRID 1621180

反応式

HRID 1621180 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 2331Benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-474a7b3a6cae4cc7a2fc1d8e651e0575
出典データセット
uspto-grants-2014_07
特許番号
US08772536B2

関連ノート

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