Hydrochloric Acid → HCID 59699543, compound

HRID 901807Notes

Reaction equation

HRID 901807 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:76][C@H:75]([CH2:77][OH:78])[C@@H:62]([O:63][C@@H:64]3[O:72][C@H:71]([CH2:73][OH:74])[C@@H:69]([OH:70])[C@H:67]([OH:68])[C@H:65]3[OH:66])[C@H:60]([OH:61])[C@H:58]2[OH:59])[C@@H:45]([CH2:79][O:80]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.Cl>CO.[OH-].[Pd+2].[OH-]>[C@@H:64]1([O:63][C@@H:62]2[C@@H:75]([CH2:77][OH:78])[O:76][C@@H:57]([O:56][C@@H:46]3[C@@H:45]([CH2:79][OH:80])[O:44][C@H:10]([O:11][C@H:12]4[C@H:16]([OH:17])[CH2:15][NH:14][C@@H:13]4[CH2:35][OH:36])[C@H:9]([OH:8])[C@H:47]3[OH:48])[C@H:58]([OH:59])[C@H:60]2[OH:61])[O:72][C@H:71]([CH2:73][OH:74])[C@@H:69]([OH:70])[C@H:67]([OH:68])[C@H:65]1[OH:66]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86602945HCID 86602945, compound

Product 1

HCID 59699543HCID 59699543, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The compound (100.7 mg, 0.084 mmol) synthesized in Example 19 (19f) was dissolved in methanol (10 mL) and 36% hydrochloric acid (280 μL) and palladium hydroxide (100 mg) were added thereto, followed by stirring of the mixture at room temperature under a hydrogen atmosphere for 4 hours. After celite filtration, 18% ammonia water (1 mL) was added thereto and the solvent was distilled off under reduced pressure. The residue was purified by ion exchange resin (Dowex 50w×8) column (water—1% ammonia water). Further, it 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 (10.0 mg, 19.2%) as a colorless solid.

Workup

  1. filtrationAfter celite filtration, 18% ammonia water (1 mL)
  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—1% ammonia water)
  5. customFurther, it was purified

Sources & evidence

ORD record
ord-4b41a8178d94464d845168885019b517
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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