HCID 86602935, compound → HCID 59699536, compound

HRID 1868181Notes

Reaction equation

HRID 1868181 reaction equation
C([O:8][C@@H:9]1[C@@H:40]([O:41]CC2C=CC=CC=2)[C@H:39]([O:49][C@H:50]2[O:79][C@H:78]([CH3:80])[C@@H:69]([O:70]CC3C=CC=CC=3)[C@H:60]([O:61]CC3C=CC=CC=3)[C@H:51]2[O:52]CC2C=CC=CC=2)[C@@H:38]([CH2:81][O:82]CC2C=CC=CC=2)[O:37][C@@H:10]1[O:11][C@H:12]1[C@H:16]([F:17])[CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[C@@H:13]1[CH2:28][O:29]CC1C=CC=CC=1)C1C=CC=CC=1>CO.Cl.[OH-].[Pd+2].[OH-].[C]>[C@H:50]1([O:49][C@@H:39]2[C@@H:38]([CH2:81][OH:82])[O:37][C@H:10]([O:11][C@H:12]3[C@H:16]([F:17])[CH2:15][NH:14][C@@H:13]3[CH2:28][OH:29])[C@H:9]([OH:8])[C@H:40]2[OH:41])[O:79][C@H:78]([CH3:80])[C@@H:69]([OH:70])[C@H:60]([OH:61])[C@H:51]1[OH:52]

Participants

4

Reactant 1

HCID 86602935HCID 86602935, compound

Product 1

HCID 59699536HCID 59699536, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

The compound (109 mg, 90.2 μmol) synthesized in Example 9 (9d) was dissolved in 1% hydrochloric acid methanol solution (5 mL) and 20% palladium hydroxide-carbon (55 mg) was added thereto, followed by stirring of the mixture under a hydrogen atmosphere for 1 hour. 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 (26 mg, 65%) 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-35b403357f204e6cb9fc88ccce163086
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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