Methyl iodide → Methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate

HRID 1968415ノート

反応式

HRID 1968415 の反応式
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI>C1COCC1>[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[N:8]2[CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 10609791HCID 10609791、化合物

生成物 1

HCID 66587141Methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

A solution of Example 2A (1 g, 4.25 mmol) in 10 mL of anhydrous THF at −78° C. was treated with 4.68 mL (4.68 mmol) of a 1 M solution of lithium bis(trimethylsilyl)amide in THF. The reaction mixture was stirred for 1 h. at about −70° C. before adding MeI (1.59 mL, 25.51 mmol). Upon complete conversion of the azetidinone, the reaction was quenched with saturated aqueous NH4Cl and partitioned between EtOAc and water. The organic layer was washed sequentially with saturated aqueous sodium bisulfite, and saturated aqueous NaCl. The resulting organic layer was dried (MgSO4) and evaporated to afford the title compound (a mixture of diasteromers) as a white solid (1.06 g, 93%); 1H NMR (CDCl3) δ 1.07/1.53 (d/d, J=7.5 Hz, 3H), 3.59/3.74 (s/s, 3H), 3.85/4.48 (q/q, J=7.5 Hz, 1H), 4.10-4.14 (m, 1H), 4.60-4.64/4.65-4.69 (m/m, 1H), 4.88-4.92/4.98-5.02 (m/m, 1H), 7.24-7.40 (m, 5H).

後処理

  1. customUpon complete conversion of the azetidinone, the reaction was quenched with saturated aqueous NH4Cl
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed sequentially with saturated aqueous sodium bisulfite, and saturated aqueous NaCl
  4. dry with materialThe resulting organic layer was dried (MgSO4)
  5. customevaporated

出典と根拠

ORDレコード
ord-06375c0a8e8c4deba35f231081032837
出典データセット
uspto-grants-2013_04
特許番号
US08426400B2

反応ノート

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