Nitrogen → (S)-2-Boc-amino-1-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol

HRID 2212233

반응식

HRID 2212233 반응식
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=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]([CH:31]([CH2:34][CH3:35])[C@@:32]([NH2:17])([C:5]1[O:1][C:2]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[N:3][N:4]=1)[OH:33])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

참가 물질

8

반응물 5

HCID 947NitrogenHCID 3283Diethyl EtherHCID 40231652-(Pyridin-3-yl)-1,3,4-oxadiazoleHCID 86590935(S)-2-Boc-aminobutyraldehydeHCID 178418339Butyllithium

생성물 1

HCID 69616467(S)-2-Boc-amino-1-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
-45 °C

실험 절차

To a stirred solution of the 3-[1,3,4]oxadiazol-2-yl-pyridine (5 g, 34 mmol) in THF (100 mL) was added HMPA (5 mL) and n-BuLi (1.6 M solution in hexane, 21.25 mL) drop wise under N2 at −78° C. After 1 h, MgBr.Et2O (8.77 g, 34 mmol) was added and the reaction mixture was allowed to warm to −45° C. for 1 h before being treated with (S)-2-Boc-amino-butyraldehyde (4.22 g, 22.1 mmol) in THF (20 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 (S)-2-Boc-amino-1-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol (1.5 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-46d6204d4526469fb0b3091387b9ca61
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101880B2

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