HCID 86602937, compound → HCID 59699527, compound

HRID 901795Notes

Reaction equation

HRID 901795 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]([CH3:87])[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]([CH2:88][O:89]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>CO.Cl.[OH-].[Pd+2].[OH-].[C]>[C@H:57]1([O:56][C@@H:46]2[C@@H:45]([CH2:88][OH:89])[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]([CH3:87])[C@@H:76]([OH:77])[C@H:67]([OH:68])[C@H:58]1[OH:59]

Participants

4

Reactant 1

HCID 86602937HCID 86602937, compound

Product 1

HCID 59699527HCID 59699527, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

The compound (58 mg, 44.7 μmol) synthesized in Example 11 (11b) was dissolved in 1% hydrochloric acid methanol solution (5 mL) and 20% palladium hydroxide-carbon (30 mg) was added thereto, followed by stirring of the mixture under a hydrogen atmosphere for 1.5 hours. After the catalyst was removed by celite filtration, 28% ammonia water (0.2 mL) was added thereto and the mixture was stirred for 10 minutes. After the solvent was distilled off under reduced pressure and it was passed through ion exchange resin (Dowex 50w×8) 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 the residue 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 (13 mg, 68%) as a colorless solid.

Workup

  1. customAfter the catalyst was removed by celite filtration, 28% ammonia water (0.2 mL)
  2. additionwas added
  3. stirringthe mixture was stirred 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. customthe residue was purified

Sources & evidence

ORD record
ord-73750e42cc784e3e87139acdd9963269
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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