HCID 86602919, compound → 736967-62-7

HRID 1868162Notes

Reaction equation

HRID 1868162 reaction equation
C([O:8][C@@H:9]1[CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[C@H:11]([CH2:24][O:25]CC2C=CC=CC=2)[C@H:10]1[O:33][C@H:34]1[O:87][C@H:86]([CH2:88][O:89]CC2C=CC=CC=2)[C@@H:53]([O:54][C@@H:55]2[O:84][C@H:83]([CH3:85])[C@@H:74]([O:75]CC3C=CC=CC=3)[C@H:65]([O:66]CC3C=CC=CC=3)[C@H:56]2[O:57]CC2C=CC=CC=2)[C@H:44]([O:45]CC2C=CC=CC=2)[C@H:35]1[O:36]CC1C=CC=CC=1)C1C=CC=CC=1>CO.Cl.[OH-].[Pd+2].[OH-].[C]>[C@@H:55]1([O:54][C@@H:53]2[C@@H:86]([CH2:88][OH:89])[O:87][C@H:34]([O:33][C@H:10]3[C@H:9]([OH:8])[CH2:13][NH:12][C@@H:11]3[CH2:24][OH:25])[C@H:35]([OH:36])[C@H:44]2[OH:45])[O:84][C@H:83]([CH3:85])[C@@H:74]([OH:75])[C@H:65]([OH:66])[C@H:56]1[OH:57]

Participants

4

Reactant 1

HCID 86602919HCID 86602919, compound

Product 1

HCID 9846130736967-62-7Yield 35.2%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

The compound (13.3 g, 10.3 mmol) synthesized in Example 2 (2g) was dissolved in 1% hydrochloric acid methanol solution (250 mL) and 20% palladium hydroxide-carbon (4 g) 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 (5 mL) was added thereto and the mixture was stirred for 10 minutes. After the solvent was distilled off under reduced pressure and the residue was passed through ion exchange resin (Dowex 50w×8) column with water (200 mL), 1% ammonia water (200 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 (1.6 g, 35%) as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-05e661fe5cde4785859fb30bc3a89134
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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