Hydrochloric Acid → HCID 11496503, compound

HRID 901799Notes

Reaction equation

HRID 901799 reaction equation
C([O:8][C@@H:9]1[C@@H:49]([O:50]CC2C=CC=CC=2)[C@H:48]([O:58][C@@H:59]2[O:88][C@H:87]([CH3:89])[C@@H:78]([O:79]CC3C=CC=CC=3)[C@H:69]([O:70]CC3C=CC=CC=3)[C@H:60]2[O:61]CC2C=CC=CC=2)[C@@H:47]([CH2:90][O:91]CC2C=CC=CC=2)[O:46][C@@H:10]1[O:11][C@@H:12]1[C@@H:19]2[C@@H:15]([N:16](C(OCC3C=CC=CC=3)=O)[O:17][CH2:18]2)[C@H:14]([O:30]CC2C=CC=CC=2)[C@@H:13]1[O:38]CC1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.Cl>CO.[OH-].[Pd+2].[OH-].[C]>[C@@H:59]1([O:58][C@@H:48]2[C@@H:47]([CH2:90][OH:91])[O:46][C@H:10]([O:11][C@@H:12]3[C@@H:19]([CH2:18][OH:17])[C@@H:15]([NH2:16])[C@H:14]([OH:30])[C@H:13]3[OH:38])[C@H:9]([OH:8])[C@H:49]2[OH:50])[O:88][C@H:87]([CH3:89])[C@@H:78]([OH:79])[C@H:69]([OH:70])[C@H:60]1[OH:61]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86602941HCID 86602941, compound

Product 1

HCID 11496503HCID 11496503, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

The compound (115 mg, 86.8 μmol) synthesized in Example 15 (15a) was dissolved in methanol (20 mL) and ethyl acetate (1 mL) and hydrochloric acid (10 μL) and 20% palladium hydroxide-carbon (115 mg) were added thereto, followed by stirring of the mixture at room temperature under a hydrogen atmosphere for 4 hours. After celite filtration, the solvent was distilled off under reduced pressure and the residue was purified by ion exchange resin (Dowex 50w×8) column (water—5% 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 (30 mg, 73%) as a colorless amorphous.

Workup

  1. filtrationAfter celite filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was purified by ion exchange resin (Dowex 50w×8) column (water—5% ammonia water)
  4. customFurther, it was purified

Sources & evidence

ORD record
ord-93cd5b93e3044e2a9173ad78cfa79280
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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