Potassium Carbonate → HCID 66775543, 화합물

HRID 1645193노트

반응식

HRID 1645193 반응식
C(OC([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[CH2:14][N:15]([C:28]([C:30]2[N:31]=[CH:32][N:33]([CH3:35])[CH:34]=2)=[O:29])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=2)[CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45]>CN(C=O)C.[Cl-].C([N+](CC)(CC)CC)C>[F:25][C:24]([F:26])([F:27])[O:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:15]([CH2:14][CH:11]1[CH:12]2[CH:10]1[CH2:9][N:8]([CH2:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH2:13]2)[C:28]([C:30]1[N:31]=[CH:32][N:33]([CH3:35])[CH:34]=1)=[O:29]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 66775648HCID 66775648, 화합물

생성물 1

HCID 66775543HCID 66775543, 화합물

시약·촉매·용매 2

HCID 5946Tetraethylammonium Chloride촉매HCID 6228Dimethylformamide용매

실험 절차

To a stirring solution of 6-{[(1-Methyl-1H-imidazole-4-carbonyl)-(3-trifluoromethoxy-benzyl)-amino]-methyl}-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester prepared above (2.63 gm, 5.63 mmol) in 30 mL DMF was added potassium carbonate (3.89 gm, 28.2 mmol), tetraethylammonium chloride (150 mg), followed by benzyl 2-bromoacetate (0.88 mL, 5.63 mmol). The reaction was stirred at room temperature for 20 hours and quenched with water. The mixture was diluted with ethyl acetate, the layers separated and the aqueous layer extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to yield 2.8 gm of crude material. The crude material was purified by flash chromatography to yield 2.7 gm of benzyl 2-(6-((N-(3-(trifluoromethoxy)benzyl)-1-methyl-1H-imidazole-4-carboxamido)methyl)-3-aza-bicyclo[3.1.0]hexan-3-yl)acetate; MS (M+1) 543.3.

후처리

  1. customquenched with water
  2. additionThe mixture was diluted with ethyl acetate
  3. customthe layers separated
  4. extractionthe aqueous layer extracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield 2.8 gm of crude material
  9. customThe crude material was purified by flash chromatography

출처 및 근거

ORD 기록
ord-b498cec23a0941b7943cfab17aad2dad
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124639B2

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