Sodium Carbonate → HCID 67163472, compound

HRID 68624Notes

Reaction equation

HRID 68624 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](=[O:28])([O-])[O-:26].[Na+].[Na+]>O.O1CCCC1.ClC(OCC1C=CC=CC=1)=O.C(OCC)(=O)C>[CH2:14]([O:26][C:25]([N:13]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=1)[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:28])[C:15]1[CH:24]=[CH:23][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 67163687HCID 67163687, compound

Product 1

HCID 67163472HCID 67163472, compoundYield 204.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 10387Benzyl chloroformateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the compound 3 (810 mg) and sodium carbonate (383 mg) in water (5 mL) and tetrahydrofuran (2 mL), benzyl chloroformate (413 μl) was added at 0° C. The reaction mixture was stirred at 0° C. for one hour. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:1) to obtain the title compound (1.16 g) having the following physical properties.

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:1)

Sources & evidence

ORD record
ord-08aaded538ae4a78a1ac4d2d83cfc1d2
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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