4-Methylmorpholine → HCID 11478231、化合物

HRID 2269346ノート

反応式

HRID 2269346 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@@H:14]([N:16]([CH:24]=[O:25])[O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH3:15])[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.Cl.[N:72]1[CH:77]=[CH:76][CH:75]=[C:74]([NH:78][C:79](=[O:86])[C@@H:80]([NH2:85])[C:81]([CH3:84])([CH3:83])[CH3:82])[CH:73]=1>CN(C=O)C>[CH3:82][C:81]([CH3:84])([CH3:83])[C@H:80]([NH:85][C:11](=[O:13])[C@H:10]([CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@@H:14]([N:16]([CH:24]=[O:25])[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[CH3:15])[C:79](=[O:86])[NH:78][C:74]1[CH:73]=[N:72][CH:77]=[CH:76][CH:75]=1

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11245009HCID 11245009、化合物HCID 70212260HCID 70212260、化合物

生成物 1

HCID 11478231HCID 11478231、化合物収率 62.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

To a solution of (2R,3S)-2-(3-phenyl-1-propyl)-3-(formyl-2-tetrahydropyrariyloxyamino)butanoic acid (120 mg, 0.344 mmol) in DMF (1 mL) is added BOP reagent (167 mg, 0.378 mmol), HOBt (51 mg, 0.378 mmol), and NMM (174 mg, 1.72 mmol). After 30 min, (2S)-2-amino-3,3-dimethylbutanoic acid 3-pyridylamide dihydrochloride (118 mg, 0.410) is added and the resulting solution is stirred at 25° C. for 18 h. The reaction mixture is concentrated, diluted with EtOAc (20 mL) and washed sequentially with 1 M aqueous sodium carbonate and saturated aqueous sodium chloride. The organic layer is dried over magnesium sulfate, concentrated in vacuo, and purified by silica gel chromatography (elution with 2:1 EtOAc-hexane) to provide (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(3-phenyl-1-propyl)butanoic acid [(1S)-2,2-dimethyl-1-(3-pyridylcarbamoyl)-1-propyl]amide as a solid (115 mg, 62% yield). ESI-MS m/z 529 (M+H)+.

後処理

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with EtOAc (20 mL)
  3. washwashed sequentially with 1 M aqueous sodium carbonate and saturated aqueous sodium chloride
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography (elution with 2:1 EtOAc-hexane)

出典と根拠

ORDレコード
ord-fade9af093a64ab393021f216af59083
出典データセット
uspto-grants-2001_12
特許番号
US06329400B1

反応ノート

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