tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate → tert-butyl 2-((2S,5R)-2-carbamoyl-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate

HRID 627240노트

반응식

HRID 627240 반응식
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[C:11]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:12][C@H:13]2[C:18](=[O:20])[NH2:19])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:18]([C@@H:13]1[CH:12]=[C:11]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C@@H:10]2[CH2:17][N:14]1[C:15](=[O:16])[N:9]2[OH:8])(=[O:20])[NH2:19]

참가 물질

4

반응물 1

HCID 89852204tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate2회

생성물 1

HCID 117940260tert-butyl 2-((2S,5R)-2-carbamoyl-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate수율 98%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate (Intermediate 227, 0.300 g, 0.72 mmol) in EtOAc (5 mL) was added 10% Pd/C (0.077 g, 0.72 mmol). The reaction mixture was stirred under hydrogen for 30 minutes. The reaction mixture was filtered through celite and washed with EtOAc. The solvent was removed in vacuo to give the title compound as a white solid (0.23 g, 98%).

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with EtOAc
  3. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-3226fa1876a445bbbe3ad8e1a9561a21
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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