Dimethylamine → (4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 2222994ノート

反応式

HRID 2222994 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH3:21][NH:22][CH3:23].O1CCCC1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[O:16])[N:22]([CH3:23])[CH3:21])[N:13]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 15020512-Amino-1,3-thiazole-4-carboxylic acid, N-BOC protected

生成物 1

HCID 86603401(4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester収率 75%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a suspension of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (prepared as described in example 15) (183 mg, 0.75 mmol) in toluene (7 mL) was added thionyl chloride (2.2 mL, 30 mmol) and the mixture heated to reflux under argon for 2.5 hours. The mixture was then concentrated in vacuo, the residue suspended in dichloromethane (7 mL), a 2 M solution of dimethylamine in tetrahydrofuran (0.5 mL, 1 mmol) added and the mixture stirred at ambient temperature under argon overnight. The reaction mixture was concentrated in vacuo, the residue suspended in ethyl acetate and the solid removed by filtration. The filtrate was concentrated in vacuo and the residue purified by chromatography over silica gel eluted with 1% v/v methanol in ethyl acetate to give (4-dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester as a colorless solid (152 mg, 75%).

後処理

  1. temperaturethe mixture heated
  2. temperatureto reflux under argon for 2.5 hours
  3. concentrationThe mixture was then concentrated in vacuo
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe solid removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue purified by chromatography over silica gel
  8. washeluted with 1% v/v methanol in ethyl acetate

出典と根拠

ORDレコード
ord-bfab370760d34f99a118583e6773039c
出典データセット
uspto-grants-2008_05
特許番号
US07371869B2

反応ノート

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