Hydrochloric Acid → HCID 67157315, compound

HRID 901796Notes

Reaction equation

HRID 901796 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[CH2:16][N:15](C(OCC2C=CC=CC=2)=O)[C@H:14]([CH2:27][O:28]CC2C=CC=CC=2)[C@H:13]1[OH:36])C1C=CC=CC=1.Cl>CO.[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[CH2:16][NH:15][C@H:14]([CH2:27][OH:28])[C@H:13]3[OH: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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86602938HCID 86602938, compound

Product 1

HCID 67157315HCID 67157315, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

The compound (90 mg, 74.6 μmol) synthesized in Example 12 (12a) was dissolved in methanol (10 mL) and hydrochloric acid (140 μL) and 20% palladium hydroxide-carbon (90 mg) were added thereto, followed by stirring of the mixture at room temperature under a hydrogen atmosphere for 2 hours. After the celite filtration, ammonia water (5%) was added thereto until the pH became neutral. 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 (26 mg, 79%) as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-f4c09bed09174beb80b26f9d98eec40b
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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