Ethyl bromopyruvate → Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

HRID 244651ノート

反応式

HRID 244651 の反応式
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C:5](=[S:7])[NH2:6])[CH3:2].Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C:5]1[S:7][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:6]=1)[CH3:2]

参加物

4

反応物 2

HCID 66144Ethyl bromopyruvateHCID 27947342,2-Diethoxythioacetamide

生成物 1

HCID 16220290Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
90 °C

実験手順

To a solution of 2,2-bis(ethyloxy)ethanethioamide (648 mg) (available from Maybridge International) in ethanol (30 ml) was added ethyl bromopyruvate (0.598 ml) in ethanol (1 ml). Powdered molecular sieves (200 mg) were added and the mixture heated at 90° C. for 18 h. The mixture was filtered, washed with ethanol (10 ml) and the solvent removed in vacuo. The residue was triturated with DCM (15 ml) and the solid removed by filtration and washed with DCM (10 ml). The filtrate was concentrated in vacuo. Purification by chromatography on silica gel (70 g cartridge; FlashMaster II) eluting with 0-50% ethyl acetate in cyclohexane over 40 min gave the title compound (455 mg) as a yellow oil.

後処理

  1. additionPowdered molecular sieves (200 mg) were added
  2. filtrationThe mixture was filtered
  3. washwashed with ethanol (10 ml)
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with DCM (15 ml)
  6. customthe solid removed by filtration
  7. washwashed with DCM (10 ml)
  8. concentrationThe filtrate was concentrated in vacuo
  9. customPurification by chromatography on silica gel (70 g cartridge; FlashMaster II)
  10. washeluting with 0-50% ethyl acetate in cyclohexane over 40 min

出典と根拠

ORDレコード
ord-f2cf7103058542448074cb347b4bec26
出典データセット
uspto-grants-2014_02
特許番号
US08658635B2

反応ノート

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