HCID 86602936, compound → HCID 67157051, compound

HRID 1868183Notes

Reaction equation

HRID 1868183 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]([O:17]CC2C=CC=CC=2)[CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[C@H:13]1[CH2:35][F:36])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]([OH:17])[CH2:15][NH:14][C@H:13]3[CH2:35][F:36])[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 86602936HCID 86602936, compound

Product 1

HCID 67157051HCID 67157051, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

The compound (53 mg, 43.9 mmol) synthesized in Example 10 (10d) 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 3 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 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 (1.6 mg, 8%) 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-95fa40ca36184808b844157785377b44
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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