Potassium Carbonate → HCID 91275795, compound

HRID 1169290Notes

Reaction equation

HRID 1169290 reaction equation
[CH2:1]([N:8]([C:27](=[O:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[CH:12][C:11]=1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>CN(C=O)C>[CH2:1]([N:8]([C:27](=[O:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[CH:12][C:11]=1[O:26][CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 91557333HCID 91557333, compound

Product 1

HCID 91275795HCID 91275795, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of Example 20C (300 mg, 0.68 mmol) in DMF (5.0 mL) was treated with K2CO3 (189 mg, 1.36 mmol) and t-butyl bromoacetate (121 μL, 0.82 mmol), heated at 75° C. for 1.5 hours, quenched with water, and extracted with ethyl acetate. The extract was washed with brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel 4:1 hexanes/ethyl acetate to provide the desired product.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-c09dd05209244e34ba4cad10c28f979f
Source dataset
uspto-grants-2003_09
Patent number
US06627767B2

Reaction notes

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