Potassium Carbonate → HCID 89668591, compound

HRID 1482240Notes

Reaction equation

HRID 1482240 reaction equation
[O:1]=[C:2]([N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C@@H:3]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](B2OC(C)(C)C(C)(C)O2)=[CH:7][CH:6]=1.Br[C:35](=[CH2:45])[CH2:36][CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.CCCCCC.C(OCC)(=O)C.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>[C:23]([O:22][C:21]([NH:20][C@H:3]([C:2](=[O:1])[N:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:35](=[CH2:45])[CH2:36][CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[CH:7][CH:6]=1)=[O:27])([CH3:26])([CH3:24])[CH3:25]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 108682574-Pentenoic acid, 4-bromo-, 1,1-dimethylethyl esterHCID 89668404HCID 89668404, compound

Product 1

HCID 89668591HCID 89668591, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl (S)-(1-oxo-1-(piperidin-1-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-yl)carbamate (Compound SP414) (3.00 g, 6.54 mmol) was dissolved in DMF (24.0 ml) and water (6.0 ml), tert-butyl 4-bromopent-4-enoate synthesized by the method described in the literature (Organic Letters, 2011, 13, 5830-5833) (2.31 g, 9.82 mmol), Pd(PPh3)4 (1.13 g, 0.978 mmol) and potassium carbonate (1.81 g, 13.10 mmol) were added and the mixture was stirred at 80° C. for 2 hours. The reaction solution was left to cool, and then diluted with hexane/ethyl acetate (1/1) and washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous ammonium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane:ethyl acetate=100:0-75:25) to afford the title compound SP415 (2.72 g, 85%).

Workup

  1. additionwere added
  2. waitThe reaction solution was left
  3. temperatureto cool
  4. washwashed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate=100:0-75:25)

Sources & evidence

ORD record
ord-8ab1b8e102cb4b24a469976c74a67b8f
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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