Methanol → 4-Aminothiazole-5-carboxylic acid ethyl ester

HRID 1161547ノート

反応式

HRID 1161547 の反応式
CO.C1COCC1.[CH2:8]([O:10][C:11]([C:13]1[S:17][C:16](S(C)(=O)=O)=[N:15][C:14]=1[NH2:22])=[O:12])[CH3:9].[BH4-].[Na+]>O.C(OCC)(=O)C>[CH2:8]([O:10][C:11]([C:13]1[S:17][CH:16]=[N:15][C:14]=1[NH2:22])=[O:12])[CH3:9]

参加物

7

反応物 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 59516885Ethyl 4-amino-2-(methylsulfonyl)-5-thiazolecarboxylate

生成物 1

HCID 190176714-Aminothiazole-5-carboxylic acid ethyl ester収率 81.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 1 liter of a methanol:THF=1:1 mixed solvent solution containing 34.5 g of 4-amino-2-methanesulfonylthiazole-5-carboxylic acid ethyl ester, 10.4 g of sodium borohydride was added in small portions over a period of 20 minutes at room temperature. The reaction mixture was stirred at room temperature for 2 hours, and then was poured into 8 liters of ethyl acetate and 4 liters of water. The organic layer was washed with 3 liters of water and 3 liters of saturated brine, and the aqueous layer was extracted with ethyl acetate again. The organic layers were combined and dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (19.3 g) as a light yellow solid.

後処理

  1. additionwas added in small portions over a period of 20 minutes at room temperature
  2. washThe organic layer was washed with 3 liters of water and 3 liters of saturated brine
  3. extractionthe aqueous layer was extracted with ethyl acetate again
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccating agent was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-ec707d28489c47b1bccd6cd1b7585fc6
出典データセット
uspto-grants-2010_10
特許番号
US07816522B2

反応ノート

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