tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamate → tert-Butyl (4-propionylthiazol-2-yl)carbamate

HRID 32816ノート

反応式

HRID 32816 の反応式
[CH2:1]([Mg]Cl)[CH3:2].[C:5]([O:9][C:10](=[O:23])[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[O:22])N(OC)C)[N:16]=1)([CH3:8])([CH3:7])[CH3:6]>O1CCCC1>[C:5]([O:9][C:10](=[O:23])[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[O:22])[CH2:1][CH3:2])[N:16]=1)([CH3:8])([CH3:6])[CH3:7]

参加物

4

反応物 2

HCID 58604314tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamateHCID 178461633HCID 178461633、化合物

生成物 1

HCID 45117897tert-Butyl (4-propionylthiazol-2-yl)carbamate収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

A solution of ethyl magnesium chloride (126 mL, 0.252 mol, 2 M in tetrahydrofuran) was stirred and cooled to −70° C. on a dry ice/acetone bath. A solution of [4-(methoxy-methyl-carbamoyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (14.5 g, 0.0504 mol) in tetrahydrofuran (200 mL) was added dropwise over approximately 5 minutes. The mixture was stirred for 1 hour. The cooling bath was removed and stirring continued for an additional 2 hours. The mixture was poured into a mixture of ice and saturated aqueous ammonium chloride solution and then extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over magnesium sulfate and evaporated to give an off white solid which was purified by chromatography over a 350 g pad of silica gel eluted with 4:1 ethyl acetate/dichloromethane to afford (4-propionyl-thiazol-2-yl)-carbamic acid tert-butyl ester (7.09 g, 55%) as an off white solid.

後処理

  1. customThe cooling bath was removed
  2. stirringstirring
  3. waitcontinued for an additional 2 hours
  4. additionThe mixture was poured into a mixture of ice and saturated aqueous ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto give an off white solid which
  10. customwas purified by chromatography over a 350 g pad of silica gel
  11. washeluted with 4:1 ethyl acetate/dichloromethane

出典と根拠

ORDレコード
ord-f960c4b0c9e1442295160d1539d03a1e
出典データセット
uspto-grants-2008_09
特許番号
US07427635B2

反応ノート

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