Potassium Carbonate → HCID 86601623, compound

HRID 271857Notes

Reaction equation

HRID 271857 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([NH:14][C@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]>COCCOC.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:7]([O:11][C:12]([NH:14][C@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:1]=[O:4])[CH:22]=2)=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 53983472HCID 53983472, compound

Product 1

HCID 86601623HCID 86601623, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 178527696HCID 178527696, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

100 ml (201 mmol) of an aqueous 2M potassium carbonate solution and 4.4 g (3.80 mmol) of tetrakis palladium are introduced into a solution containing 33 g (77.3 mmol) of methyl (R)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxyphenyl)propionate, and 15 g (100 mmol) of 3-boronic acid-benzaldehyde (Example 28b) in 300 ml of ethylene glycol dimethyl ether. The reaction medium is heated at 85° C. for 20 h and, after a return to ambient temperature, extracted with ethyl acetate. The organic phase is washed with water and then 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 a 7/3 heptane/ethyl acetate mixture. 10.2 g of coupled product are obtained with a 35% yield.

Workup

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

Sources & evidence

ORD record
ord-043578fe9d47433a91e8bf99c4dc3215
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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