Potassium Carbonate → HCID 86601626, compound

HRID 1157498Notes

Reaction equation

HRID 1157498 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:30]([O:29][C:27]([NH:26][CH:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:1]=[O:4])[CH:9]=2)=[CH:9][CH:10]=1)[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 21988858HCID 21988858, compound

Product 1

HCID 86601626HCID 86601626, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178527696HCID 178527696, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

23 ml (45.9 mmol) of an aqueous 2M potassium carbonate solution and 1.77 g (1.50 mmol) of tetrakis palladium are introduced into a solution containing 6.64 g (15.3 mmol) of benzyl 3-(4-bromophenyl)-2-tert-butoxycarbonylaminopropionate and 3.45 g (23 mmol) of 3-boronic acid-benzaldehyde (Example 28b) in 75 ml of toluene. The reaction medium is heated at 80° C. for 20 h and, after a return to ambient temperature, extracted with ethyl acetate. The organic phase is washed with a saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue obtained is purified by chromatography on a column of silica and eluted with an 8/2 heptane/ethyl acetate mixture. 5.0 g of coupled product are obtained with a 71% yield.

Workup

  1. extractionafter a return to ambient temperature, extracted with ethyl acetate
  2. washThe organic phase is washed with a saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with an 8/2 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-35ab810e50f84cfeb60739ef51967c8b
Source dataset
uspto-grants-2010_10
Patent number
US07807669B2

Reaction notes

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