Potassium Carbonate → HCID 58653672, compound

HRID 1676035Notes

Reaction equation

HRID 1676035 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][C:15]([OH:17])=[O:16].C(=O)([O-])[O-].[K+].[K+].[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1>CS(C)=O>[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:37][C:2]2[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:5]=[CH:6][CH:7]=2)[NH:12][CH:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][C:15]([OH:17])=[O:16])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 69189DL-beta-PhenylalanineHCID 754524-MethoxybenzylamineHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 58653672HCID 58653672, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2,6-difluoronitrobenzene (200 mg, 1.26 mmol) in DMSO (2 mL) was added 3-amino-3-phenylpropionic acid (228 mg, 1.39 mmol) and potassium carbonate (347 mg, 2.52 mmol). The suspension was heated to 100° C. for 0.5 hour, and 4-methoxybenzylamine (180 μL, 1.39 mmol) was added, and heating continued for a further 3 hours. The suspension was cooled to room temperature, and partitioned between water and ethyl acetate. The aqueous layer was acidified with dilute hydrochloric acid (pH<4), and then extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (19:1) to afford the title compound, [LCMS (Method A, Mobile Phase II) RT=4.75 min, MH+ 422].

Workup

  1. temperatureheating
  2. temperatureThe suspension was cooled to room temperature
  3. custompartitioned between water and ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with a mixture of dichloromethane and methanol (19:1)

Sources & evidence

ORD record
ord-ea54982910114730a3b3ef8beb1db5ee
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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