Potassium Carbonate → (R)-[3-oxo-1-(2,4,5-trifluoro-benzyl)-3-(1-bromo-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-propyl]-carbamic acid tert-butyl ester

HRID 221428노트

반응식

HRID 221428 반응식
[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=1[F:34])[CH2:9][C:10](=[O:24])[N:11]1[CH2:16][CH2:15][N:14]2[C:17]([C:20]([F:23])([F:22])[F:21])=[N:18][CH:19]=[C:13]2[CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[Br:36]N1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(O)C>[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:27]=1[F:34])[CH2:9][C:10](=[O:24])[N:11]1[CH2:16][CH2:15][N:14]2[C:17]([C:20]([F:22])([F:21])[F:23])=[N:18][C:19]([Br:36])=[C:13]2[CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 90495Di-tert-butyl dicarbonateHCID 57518397(R)-[3-oxo-1-(2,4,5-trifluoro-benzyl)-3-(3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-propyl]-carbamic acid tert-butyl ester

생성물 1

HCID 57518400(R)-[3-oxo-1-(2,4,5-trifluoro-benzyl)-3-(1-bromo-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-propyl]-carbamic acid tert-butyl ester수율 86.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(R)-[3-oxo-1-(2,4,5-trifluoro-benzyl)-3-(3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-propyl]-carbamic acid tert-butyl ester 1l (20.0 g, 39.6 mmol) was dissolved in 300 mL of anhydrous ethanol under stirring, and 1-bromo-2,5-pyrrolidinedione (14.1 g, 79.2 mmol) was then added to the solution at room temperature. After stirring for an hour, potassium carbonate (10.9 g, 79.2 mmol) and di-tert-butyl dicarbonate (8.6 g, 39.6 mmol) were added to the mixture, and the mixture was stirred for an hour and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was filtered through a pad of coarse silica gel to remove potassium carbonate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (R)-[3-oxo-1-(2,4,5-trifluoro-benzyl)-3-(1-bromo-3-trifluoromethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazin-7-yl)-propyl]-carbamic acid tert-butyl ester 1m (20.0 g, yield 86%) as a white solid.

후처리

  1. stirringAfter stirring for an hour
  2. stirringthe mixture was stirred for an hour
  3. filtrationThe reaction mixture was filtered through a pad of coarse silica gel
  4. customto remove potassium carbonate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3aa4535210ed42bb9cbd79c9d540b63f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207161B2

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