Nitrogen → HCID 69450382, 화합물

HRID 1444582노트

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HRID 1444582 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:11][CH:10]=[N:9][N:8]=2)=[CH:3][CH:2]=1.[Li]CCCC.[N:17]#N.CCOCC.[C:24]([C:31](N)([CH2:34][CH3:35])[CH:32]=[O:33])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[C:24]([C@@H:31]([CH2:34][CH3:35])[C:32]([NH2:17])([C:10]1[O:11][C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[N:8][N:9]=1)[OH:33])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

참가 물질

8

반응물 5

HCID 947NitrogenHCID 3283Diethyl EtherHCID 7756364-(1,3,4-Oxadiazol-2-yl)pyridineHCID 86593164HCID 86593164, 화합물HCID 178418339Butyllithium

생성물 1

HCID 69450382HCID 69450382, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 12679Hexamethylphosphoramide용매

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온도
-45 °C

실험 절차

To a stirred solution of the 5-pyridin-4-yl-[1.3.4]oxadiazole (11.5 g, 78.2 mmol) in THF (300 mL) was added HMPA (5 ML) and n-BuLi (1.6 M solution in 48.9 mL of hexane) dropwise under N2 at −78° C. After 1 h, MgBr.Et2O (20.2 g, 78.2 mmol) was added and the reaction mixture was allowed to warm to −45° C. for 1 h before being treated with 2-Boc-amino-butyraldehyde (9.7 g, 50.8 mmol) in THF (50 mL). The reaction mixture was stirred for 1 h, quenched with saturated NH4Cl, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield 2(S)-Boc-amino-1-(5-pyridin-4-yl-[1.3.4]oxadiazol-2-yl)-butan-1-ol (3.5 g).

후처리

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography

출처 및 근거

ORD 기록
ord-3f74fc200d6343798621d7f46411e682
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662849B2

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