Sodium Carbonate → HCID 66905158, compound

HRID 1692089Notes

Reaction equation

HRID 1692089 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](OS(C(F)(F)F)(=O)=O)[CH:5]=[CH:6][C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]2)[C:10]1=[O:31].[CH3:40][O:41][C:42]([C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1)=[O:43].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.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>[CH3:40][O:41][C:42]([C:44]1[CH:49]=[CH:48][C:47]([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][C@@H:9]3[CH2:13][CH2:12][N:11]([N:14]4[CH2:19][CH2:18][CH:17]([O:20][Si:21]([CH:25]([CH3:27])[CH3:26])([CH:28]([CH3:30])[CH3:29])[CH:22]([CH3:23])[CH3:24])[CH2:16][CH2:15]4)[C:10]3=[O:31])=[C:2]([Cl:1])[CH:3]=2)=[CH:46][CH:45]=1)=[O:43]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 86630016HCID 86630016, compound

Product 1

HCID 66905158HCID 66905158, compoundYield 93.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Bring a mixture of trifluoro-methanesulfonic acid 3-Chloro-4-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-phenyl ester (0.83 g, 1.35 mmol), 4-methoxycarbonylphenylboronic acid (0.29 g, 1.62 mmol), sodium carbonate (0.43 g, 4.06 mmol) in THF (20 mL) and water (6 mL) to 60° C. To the mixture at 60° C., add Pd(PPh3)4 (0.08 g, 0.07 mmol). Raise the reaction temperature to 80° C. and stir for 1 hour. Cool the reaction, dilute with ethyl acetate, and wash with water and brine. Dry the organic layer with Na2SO4, remove the solvent in vacuo, and purify on silica gel column with 0% to 50% ethyl acetate in hexanes gradient to afford 0.76 g (93%) of the titled product. MS (m/z): 599 (M+).

Workup

  1. temperatureCool
  2. customthe reaction
  3. washwash with water and brine
  4. dry with materialDry the organic layer with Na2SO4
  5. customremove the solvent in vacuo
  6. custompurify on silica gel column with 0% to 50% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-5d8811630f9843c88f96f8b34c3ee381
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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