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

HRID 1170514노트

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HRID 1170514 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52e89bc613294643ba254eabd0ffe2bc
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825256B2

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