Lithium Chloride → HCID 89996171、化合物

HRID 2276045ノート

反応式

HRID 2276045 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][Cl:9])[C:5](I)=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[Li+].[Cl-].[C:18]([N:25]1[CH2:28][C:27](=[O:29])[CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>C1COCC1>[C:21]([O:20][C:18]([N:25]1[CH2:28][C:27]([C:5]2[C:6]([CH2:8][Cl:9])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:29])[CH2:26]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

参加物

6

反応物 4

HCID 433294Lithium ChlorideHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 89996174HCID 89996174、化合物HCID 178418918HCID 178418918、化合物

生成物 1

HCID 89996171HCID 89996171、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 6-chloro-2-chloromethyl-3-iodo-pyridine (2.5 g, 8.7 mmol, 1 eq) in dry THF (25 mL) was added i-PrMgCl.LiCl complex (1.3M in THF, 7.37 mL, 9.6 mmol, 1.1 eq) at −20° C. in drop wise manner over period of 10 minutes. Pre-dissolved solution of N-boc-3-azetidinone (1.78 g, 10.4 mmol, 1.2 eq) in dry THF (10 mL) was added at −20° C. to above reaction mixture. Resulting reaction mixture was stirred at room temperature for 16 hours under nitrogen atmosphere. After maximum consumption of starting material, reaction mixture was cooled to 0° C., quenched with 10% citric acid solution (20 mL) and extracted with ethyl acetate (3×100 mL). Combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get brown oil (4.5 g, crude). Crude of title compound was used as such for next reaction. LC-MS (m/z): 332.9 (M+H).

後処理

  1. customResulting
  2. customreaction mixture
  3. customAfter maximum consumption of starting material, reaction mixture
  4. temperaturewas cooled to 0° C.
  5. customquenched with 10% citric acid solution (20 mL)
  6. extractionextracted with ethyl acetate (3×100 mL)
  7. dry with materialCombined organic phase was dried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto get brown oil (4.5 g, crude)

出典と根拠

ORDレコード
ord-0954f20113da420d9c1d6887171b8abd
出典データセット
uspto-grants-2015_09
特許番号
US09131697B2

反応ノート

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