Bis-(1H-imidazol-2-YL)-methanone → ethyl (4R)-2-oxo-1,3-thiazolidine-4-carboxylate

HRID 2215081ノート

反応式

HRID 2215081 の反応式
[NH2:1][C@@H:2]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][SH:4].[C:10](C1NC=CN=1)(C1NC=CN=1)=[O:11]>C1COCC1>[O:11]=[C:10]1[NH:1][C@H:2]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][S:4]1

参加物

4

反応物 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 10964674HCID 10964674、化合物

生成物 1

HCID 477571ethyl (4R)-2-oxo-1,3-thiazolidine-4-carboxylate収率 169.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-1 (8.5 g, 22.6 mmol) in 200 mL THF was added of carbonyl diimidazole (12.5 g) and the solution was stirred overnight at room temperature. The solution was concentrated in vacuo, 200 mL of 5% Na2CO3 was added and the solution stirred for one hour whereupon 6M HCl was added until the pH of the solution remained at 2. The solution was extracted with EtOAc, the organic phases were then combined, dried over MgSO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 40% EtOAc/hexanes to yield 6.7 g of 3-2 as a colorless oil. 1H NMR (400 MHz, acetone-d6): δ 7.5 (br s, 1H), 4.5 (dd, 1H), 4.2 (q, 2H), 3.8 (dd, 1H), 3.6 (dd, 1H), 1.2 (t, 3H).

後処理

  1. concentrationThe solution was concentrated in vacuo, 200 mL of 5% Na2CO3
  2. additionwas added
  3. stirringthe solution stirred for one hour whereupon 6M HCl
  4. additionwas added until the pH of the solution
  5. extractionThe solution was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe compound was purified by flash chromatography

出典と根拠

ORDレコード
ord-8db284ef410640a9afa0edb4ec88ab74
出典データセット
uspto-grants-2006_09
特許番号
US07109223B2

反応ノート

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