Water → HCID 67158248, compound

HRID 901783Notes

Reaction equation

HRID 901783 reaction equation
C([O:8][C@@H:9]1[C@@H:13]2[NH:14][C@H:15]([CH2:16][OH:17])[C@H:10]1[O:11][C@@H:12]2[O:18][CH3:19])C1C=CC=CC=1.C(=O)([O-])O.[Na+].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].O>CO.[OH-].[Pd+2].[OH-].[C]>[CH2:29]([O:28][C:26]([N:14]1[C@H:15]([CH2:16][OH:17])[C@@H:10]2[C@H:9]([OH:8])[C@H:13]1[C@H:12]([O:18][CH3:19])[O:11]2)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 67157265HCID 67157265, compound

Product 1

HCID 67158248HCID 67158248, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

The compound (930 mg, 3.51 mmol) synthesized in Example 7 (7a) was dissolved in methanol (20 mL) and 20% palladium hydroxide-carbon (280 mg) was added thereto, followed by stirring of the mixture under a hydrogen atmosphere for 6 hours. After the catalyst was removed by celite filtration, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate:saturated aqueous sodium hydrogencarbonate solution (2:1, 20 mL) and benzyl chloroformate (0.75 mL, 5.27 mmol) was added thereto, followed by stirring of the mixture at 0° C. for 2 hours. After water (20 mL) was added thereto at 0° C. and the mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine (20 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 1:1-3:1, V/V) to obtain the desired title compound (759 mg, yield 70%) as a colorless solid.

Workup

  1. customAfter the catalyst was removed by celite filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. stirringby stirring of the mixture at 0° C. for 2 hours
  5. extractionat 0° C. and the mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with saturated brine (20 mL)
  7. dry with materialdried with anhydrous sodium sulfate
  8. distillationby distilling off of the solvent under reduced pressure
  9. customThe residue was purified

Sources & evidence

ORD record
ord-2ffb7c38c1ca4062af8166f667da313f
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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