3-Methylpyridine → (2S,5R)-6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

HRID 73503

반응식

HRID 73503 반응식
N1C=CC=C(C)C=1.C(O)(=O)[C:9](O)=[O:10].[CH2:14]([O:21][NH:22][C@H:23]1[CH2:28][NH:27][C@H:26]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:25][CH2:24]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCl.O>[CH2:32]([O:31][C:29]([C@@H:26]1[CH2:25][CH2:24][C@@H:23]2[CH2:28][N:27]1[C:9](=[O:10])[N:22]2[O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

참가 물질

7

반응물 4

HCID 79703-MethylpyridineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 70673933Benzyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate oxalate

생성물 1

HCID 57389438(2S,5R)-6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

3-picoline (45 ml, 464, 4 eq) was added to a slurry of benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (50 g, 116 mmol, 1 eq) in dichloromethane (1000 ml) at 0° C., followed by a solution of triphosgene (31.0 g, 104.4 mmol, 0.9 eq) in dichloromethane (200 ml). The mixture was stirred at 0° C. until the reaction was deemed to be complete. The reaction was quenched with a solution of sodium bicarbonate (24.4 g, 290 mmol, 2.5 eq) in water (300 ml), and the layers were separated. The aqueous layer was extracted with dichloromethane (100 ml) and the combined organic layers were washed with water. The organic layer was concentrated in vacuo to give (2S,5R)-6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester as a solution in dichloromethane.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (100 ml)
  3. washthe combined organic layers were washed with water
  4. concentrationThe organic layer was concentrated in vacuo

출처 및 근거

ORD 기록
ord-338dc3c7bae043a6b4044df29382baec
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829191B2

연결된 노트

불러오는 중…