Potassium Carbonate → HCID 87228887, compound

HRID 2066424Notes

Reaction equation

HRID 2066424 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:26]=[C:25]4[C:21]([C:22]([C:35]#[C:36][Si](C)(C)C)=[N:23][N:24]4[CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:35]([C:22]1[C:21]2[C:25](=[CH:26][C:18]([C:15]3[CH:14]=[CH:13][C:12]([NH:11][C:9]([NH:8][C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)=[O:10])=[CH:17][CH:16]=3)=[CH:19][CH:20]=2)[N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[N:23]=1)#[CH:36]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66995078HCID 66995078, compound

Product 1

HCID 87228887HCID 87228887, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of Example 21B (660 mg) in 50 ml methanol was treated with excess K2CO3, stirred at 50° C. for 1 hour, then concentrated to ca. 2 mL and partitioned between ethyl acetate and brine. The aqueous layer was back extracted with ethyl acetate, the combined organic extracts were dried (MgSO4) and concentrated and the residue was purified via silica gel chromatography eluting with 0 to 0.75% methanol in CH2Cl2. to afford the title compound.

Workup

  1. concentrationconcentrated to ca. 2 mL
  2. custompartitioned between ethyl acetate and brine
  3. extractionThe aqueous layer was back extracted with ethyl acetate
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified via silica gel chromatography
  7. washeluting with 0 to 0.75% methanol in CH2Cl2

Sources & evidence

ORD record
ord-c280bb24424e475dbd9ab42be72d319f
Source dataset
uspto-grants-2012_10
Patent number
US08293738B2

Reaction notes

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