Ethyl Acetate → HCID 11626695, compound

HRID 1868163Notes

Reaction equation

HRID 1868163 reaction equation
C([O:8][C@@H:9]1[C@@H:47]([O:48]CC2C=CC=CC=2)[C@H:46]([O:56][C@@H:57]2[O:86][C@H:85]([CH2:87][O:88]CC3C=CC=CC=3)[C@@H:76]([O:77]CC3C=CC=CC=3)[C@H:67]([O:68]CC3C=CC=CC=3)[C@H:58]2[O:59]CC2C=CC=CC=2)[C@@H:45]([CH2:96][O:97]CC2C=CC=CC=2)[O:44][C@@H:10]1[O:11][C@H:12]1[C@H:16]([O:17]CC2C=CC=CC=2)[CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[C@@H:13]1[CH2:35][O:36]CC1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.Cl.CO>CO.[OH-].[Pd+2].[OH-].[C]>[C@@H:57]1([O:56][C@@H:46]2[C@@H:45]([CH2:96][OH:97])[O:44][C@H:10]([O:11][C@H:12]3[C@H:16]([OH:17])[CH2:15][NH:14][C@@H:13]3[CH2:35][OH:36])[C@H:9]([OH:8])[C@H:47]2[OH:48])[O:86][C@H:85]([CH2:87][OH:88])[C@@H:76]([OH:77])[C@H:67]([OH:68])[C@H:58]1[OH:59]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21893726Hydrochloride methanolHCID 86602920HCID 86602920, compound

Product 1

HCID 11626695HCID 11626695, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

The compound (611 mg, 0.55 mmol) synthesized in Example 3 (3c) was dissolved in methanol (8 mL) and ethyl acetate (2 mL) and hydrochloric acid-methanol solution (2 mL) and 20% palladium hydroxide-carbon (400 mg) were added thereto, followed by stirring of the mixture at room temperature under a hydrogen atmosphere for 4 hours. After the celite filtration, the solvent was distilled off under reduced pressure and methanol (2 mL) and 28% ammonia water (300 μL) were added thereto, followed by stirring of the mixture at room temperature for 10 minutes. After the solvent was distilled off under reduced pressure, the residue was purified by ion exchange resin (Dowex 50w×8) column (water −1.4% ammonia water). Further, it was purified using silica gel flash column chromatography (ethyl acetate:methanol:water, 1:1:1, V/V) to obtain the desired title compound (54 mg, 42%) as colorless amorphous matter.

Workup

  1. filtrationAfter the celite filtration
  2. distillationthe solvent was distilled off under reduced pressure and methanol (2 mL) and 28% ammonia water (300 μL)
  3. additionwere added
  4. stirringby stirring of the mixture at room temperature for 10 minutes
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was purified by ion exchange resin (Dowex 50w×8) column (water −1.4% ammonia water)
  7. customFurther, it was purified

Sources & evidence

ORD record
ord-7c52b8143db343b8a8b498992b1cd259
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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