Citric Acid → HCID 66990569, compound

HRID 454650Notes

Reaction equation

HRID 454650 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9]Br.[CH2:11]([O:18][C:19]1[CH:46]=[C:45]([OH:47])[CH:44]=[CH:43][C:20]=1[C:21]([NH:23][C:24]1[CH:36]=[C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:34]=[CH:33][C:25]=1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C.CN(C)C=O>[CH2:11]([O:18][C:19]1[CH:46]=[C:45]([O:47][CH2:9][CH2:8][Br:7])[CH:44]=[CH:43][C:20]=1[C:21]([NH:23][C:24]1[CH:36]=[C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:34]=[CH:33][C:25]=1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 66990773HCID 66990773, compound

Product 1

HCID 66990569HCID 66990569, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Potassium carbonate (1.6 g) and 1,2-dibromoethane (2.6 mL) were added to a N,N-dimethylformamide (5.0 mL) solution of tert-butyl 2-(2-(benzyloxy)-4-hydroxybenzamido)-4-phenylbenzoate (0.29 g), followed by stirring at 120° C. for 1 hour and 45 minutes. The reaction mixture was cooled to room temperature, and a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-91% hexane/ethyl acetate] to obtain 0.19 g of tert-butyl 2-(2-(benzyloxy)-4-(2-bromoethoxy)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-91% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-e8bbcfee18594986b4e51f21a0739357
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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