Potassium Carbonate → HCID 66775543, compound

HRID 1645193Notes

Reaction equation

HRID 1645193 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 66775543HCID 66775543, compound

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b498cec23a0941b7943cfab17aad2dad
Source dataset
uspto-grants-2012_02
Patent number
US08124639B2

Reaction notes

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