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Hydrochloric Acid → HCID 59699534, compound

HRID 901777
Notes
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Reaction equation

HRID 901777 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:86][C@H:85]([CH2:87][F:88])[C@@H:76]([O:77]CC3C=CC=CC=3)[C@H:67]([O:68]CC3C=CC=CC=3)[C@H:58]2[O:59]CC2C=CC=CC=2)[C@@H:45]([CH2:89][F:90])[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]>[F:88][CH2:87][C@H:85]1[O:86][C@@H:57]([O:56][C@@H:46]2[C@@H:45]([CH2:89][F:90])[O:44][C@H:10]([O:11][C@H:12]3[C@H:16]([OH:17])[CH2:15][NH:14][C@@H:13]3[CH2:35][OH:36])[C@H:9]([OH:8])[C@H:47]2[OH:48])[C@H:58]([OH:59])[C@@H:67]([OH:68])[C@@H:76]1[OH:77]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86602925HCID 86602925, compound

Product 1

HCID 59699534HCID 59699534, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

The compound (122.6 mg, 0.10 mmol) synthesized in Example 5 (5e) was dissolved in methanol (10 mL) containing 1% aqueous hydrochloric acid solution and 20% palladium hydroxide-carbon (100 mg) was added thereto, followed by stirring of the mixture under a hydrogen atmosphere for 2 hours. After the catalyst was removed by celite filtration, 28% ammonia water (0.5 mL) was added thereto and the mixture was stirred for 10 minutes. After the solvent was distilled off under reduced pressure and the aqueous solution (100 mL) was subjected to ion exchange resin (Dowex 50w×8) column, it was eluted with 1% ammonia water (100 mL). 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 (25.9 mg, 56%) as a colorless solid.

Workup

  1. additionwas added
  2. customAfter the catalyst was removed by celite filtration, 28% ammonia water (0.5 mL)
  3. additionwas added
  4. stirringthe mixture was stirred for 10 minutes
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. washwas eluted with 1% ammonia water (100 mL)
  7. concentrationThe ammonia water containing the desired compound was concentrated under reduced pressure
  8. customthe residue was purified

Sources & evidence

ORD record
ord-ce5da49be4654753a4f6bd372fd6a466
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07361744B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes