Nitrogen → HCID 69616463、化合物

HRID 2212232ノート

反応式

HRID 2212232 の反応式
[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]([CH: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]

参加物

8

反応物 5

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

生成物 1

HCID 69616463HCID 69616463、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
-45 °C

実験手順

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 (S)-2-Boc-amino-1-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol (3.5 g).

後処理

  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

出典と根拠

ORDレコード
ord-48953253fec8458e977331779e31231e
出典データセット
uspto-grants-2006_09
特許番号
US07101880B2

反応ノート

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