Potassium Carbonate → Benzyl 2-(3-amino-1,2,4-thiadiazol-5-YL)pyrrolidine-1-carboxylate

HRID 1170514ノート

反応式

HRID 1170514 の反応式
Br.[CH2:2]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[S:21][N:20]=[C:19]([NH:22]C(=O)C)[N:18]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[CH2:2]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[S:21][N:20]=[C:19]([NH2:22])[N:18]=1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 2

HCID 11430Potassium CarbonateHCID 686956592-(3-Acetylamino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester hydrobromide

生成物 1

HCID 53436030Benzyl 2-(3-amino-1,2,4-thiadiazol-5-YL)pyrrolidine-1-carboxylate収率 94%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

2-(3-Acetylamino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester hydrobromide (14.0 g, 37.8 mmol) was dissolved in ethanol (80 mL). The reaction mixture was cooled to 0° C. and a solution of K2CO3 (15.0 g, 108.7 mmol) in H2O (40 mL) was added. The solution was allowed to return to room temperature while stirring for 30 mins. The solution was concentrated down, redissolved in water (100 mL) and extracted with DCM (3×50 mL). The organic layers were combined and washed with brine (3×50 mL). The organic layer was partitioned from the aqueous layer, dried over MgSO4 and concentrated under vacuo to afford 9.4 g (94%) of 2-(3-amino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester as a yellow oil.

後処理

  1. customto return to room temperature
  2. concentrationThe solution was concentrated down
  3. dissolutionredissolved in water (100 mL)
  4. extractionextracted with DCM (3×50 mL)
  5. washwashed with brine (3×50 mL)
  6. customThe organic layer was partitioned from the aqueous layer
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under vacuo

出典と根拠

ORDレコード
ord-52e89bc613294643ba254eabd0ffe2bc
出典データセット
uspto-grants-2010_11
特許番号
US07825256B2

反応ノート

読み込み中…