Formaldehyde → Benzyl 2-(3-(1H-imidazol-1-YL)-1,2,4-thiadiazol-5-YL)pyrrolidine-1-carboxylate

HRID 1170515ノート

反応式

HRID 1170515 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[S:20][N:19]=[C:18]([NH2:21])[N:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]([CH:24]=O)=O.[Cl-].[NH4+:27].P([O-])([O-])([O-])=O.[Ca+2].P([O-])([O-])([O-])=O.[Ca+2].[Ca+2].[CH2:41]=O>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[S:20][N:19]=[C:18]([N:21]2[CH:24]=[CH:22][N:27]=[CH:41]2)[N:17]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 712FormaldehydeHCID 7860GlyoxalHCID 24456Tricalcium PhosphateHCID 25517Ammonium ChlorideHCID 53436030Benzyl 2-(3-amino-1,2,4-thiadiazol-5-YL)pyrrolidine-1-carboxylate

生成物 1

HCID 53436029Benzyl 2-(3-(1H-imidazol-1-YL)-1,2,4-thiadiazol-5-YL)pyrrolidine-1-carboxylate収率 66%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-(3-Amino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester (9.40 g, 30.9 mmol) was dissolved in ethanol (80 mL), glyoxal (40% wt) (19.6 g, 101.4 mmol) was added to the reaction and the solution was refluxed to 3 hours. Ammonium chloride (7.80 g, 146 mmol) and calcium phosphate (11.0 g, 110 mmol) were added followed by subsequent addition of formalin (11.0 g of a 40% aqueous solution, 147 mmol) while the reaction was maintained at reflux for 16 hours. The solution was concentrated under vacuo. The crude residue was dissolved in water (20 mL) and washed with ethyl acetate (15 mL). The aqueous layer was basified to pH=9 with 1N NaOH. The aqueous layer was then extracted with ethyl acetate (2×100 mL). The organic layers were combined and concentrated under vacuo to afford 7.2 g (66%) of 2-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester as red oil.

後処理

  1. temperaturethe solution was refluxed to 3 hours
  2. temperaturewas maintained
  3. temperatureat reflux for 16 hours
  4. concentrationThe solution was concentrated under vacuo
  5. dissolutionThe crude residue was dissolved in water (20 mL)
  6. washwashed with ethyl acetate (15 mL)
  7. extractionThe aqueous layer was then extracted with ethyl acetate (2×100 mL)
  8. concentrationconcentrated under vacuo

出典と根拠

ORDレコード
ord-4bfdc6c764474df8a56cbdb402f7cd16
出典データセット
uspto-grants-2010_11
特許番号
US07825256B2

反応ノート

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