4-Methylmorpholine → HCID 11478231, 화합물

HRID 2269346노트

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HRID 2269346 반응식
[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

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11245009HCID 11245009, 화합물HCID 70212260HCID 70212260, 화합물

생성물 1

HCID 11478231HCID 11478231, 화합물수율 62.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-fade9af093a64ab393021f216af59083
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329400B1

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