HCID 86602932, compound → HCID 59699544, compound

HRID 1868177Notes

Reaction equation

HRID 1868177 reaction equation
C([O:8][C@@H:9]1[C@@H:56]([O:57]CC2C=CC=CC=2)[C@H:55]([O:65][C@@H:66]2[O:95][C@H:94]([CH3:96])[C@@H:85]([O:86]CC3C=CC=CC=3)[C@H:76]([O:77]CC3C=CC=CC=3)[C@H:67]2[O:68]CC2C=CC=CC=2)[C@@H:54]([CH2:97][O:98]CC2C=CC=CC=2)[O:53][C@@H:10]1[O:11][C@H:12]1[C@H:16]([O:17]CC2C=CC=CC=2)[C@@H:15]([CH2:25][O:26]CC2C=CC=CC=2)[N:14](C(OCC2C=CC=CC=2)=O)[C@@H:13]1[CH2:44][O:45]CC1C=CC=CC=1)C1C=CC=CC=1>CO.Cl.[OH-].[Pd+2].[OH-].[C]>[C@@H:66]1([O:65][C@@H:55]2[C@@H:54]([CH2:97][OH:98])[O:53][C@H:10]([O:11][C@H:12]3[C@H:16]([OH:17])[C@@H:15]([CH2:25][OH:26])[NH:14][C@@H:13]3[CH2:44][OH:45])[C@H:9]([OH:8])[C@H:56]2[OH:57])[O:95][C@H:94]([CH3:96])[C@@H:85]([OH:86])[C@H:76]([OH:77])[C@H:67]1[OH:68]

Participants

4

Reactant 1

HCID 86602932HCID 86602932, compound

Product 1

HCID 59699544HCID 59699544, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

The compound (218 mg, 0.15 mmol) synthesized in Example 7 (7f) was dissolved in 1% hydrochloric acid methanol solution (5 mL) and 20% palladium hydroxide-carbon (110 mg) was added thereto, followed by stirring of the mixture under a hydrogen atmosphere for 2 hours. After the catalyst was removed by celite filtration, 28% ammonia water (0.8 mL) was added thereto, followed by stirring of the mixture for 10 minutes. After the solvent was distilled off under reduced pressure and it was passed through ion exchange resin column with water (30 mL), 1% ammonia water (30 mL) was flowed through. The ammonia water containing the desired compound was concentrated under reduced pressure and was purified using silica gel flash column chromatography (ethyl acetate:methanol:water, 5:2:1-1:1:1, V/V) to obtain the desired title compound (47 mg, 64%) as a colorless solid.

Workup

  1. customAfter the catalyst was removed by celite filtration, 28% ammonia water (0.8 mL)
  2. additionwas added
  3. stirringby stirring of the mixture for 10 minutes
  4. distillationAfter the solvent was distilled off under reduced pressure and it
  5. concentrationThe ammonia water containing the desired compound was concentrated under reduced pressure
  6. customwas purified

Sources & evidence

ORD record
ord-4179b81c361c4c379e5e432cdead6398
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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