Potassium Carbonate → HCID 66775543、化合物

HRID 1645193ノート

反応式

HRID 1645193 の反応式
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]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 66775648HCID 66775648、化合物

生成物 1

HCID 66775543HCID 66775543、化合物

試薬・触媒・溶媒 2

HCID 5946Tetraethylammonium Chloride触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b498cec23a0941b7943cfab17aad2dad
出典データセット
uspto-grants-2012_02
特許番号
US08124639B2

反応ノート

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