Hydrochloric Acid → HCID 58708323, compound

HRID 347329Notes

Reaction equation

HRID 347329 reaction equation
C([O:9][C@@H:10]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@H:11](OCC(OC(C)(C)C)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)C1C=CC=CC=1.[OH-].[Na+].Cl.F[C:37](F)(F)[C:38]([OH:40])=[O:39]>CO>[C:27]1([C@H:10]2[C@@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:40][C:38](=[O:39])[CH2:37][O:9]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 11996005HCID 11996005, compound

Product 1

HCID 58708323HCID 58708323, compoundYield 266.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 6X (2.94 g, 6.79 mmol) was added a solution of sodium hydroxide (326 mg, 8.15 mmol) in methanol (27.2 ml). After stirring for 20 h at rt, 37% hydrochloric acid (669 μl, 8.15 mmol) was added. After concentration in vacuo, a 0.4 M solution of hydrochloric acid (50 ml) was added. The resultant product (hydroxy carboxylic acid) was extracted with ethyl acetate four times and the organic layer was dried over anhydrous sodium sulfate. After concentration, the residue was dissolved in toluene (34 ml) followed by addition of trifluoroacetic acid (105 μl, 1.36 mmol). After stirring for 6 h at 80° C., the reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (eluted with 6:1 hexane:AcOEt) to give 2X (921 mg, 53%) as a white solid.

Workup

  1. concentrationAfter concentration in vacuo
  2. additiona 0.4 M solution of hydrochloric acid (50 ml) was added
  3. extractionThe resultant product (hydroxy carboxylic acid) was extracted with ethyl acetate four times
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter concentration
  6. dissolutionthe residue was dissolved in toluene (34 ml)
  7. stirringAfter stirring for 6 h at 80° C.
  8. concentrationthe reaction mixture was concentrated in vacuo
  9. customthe residue was purified by silica gel chromatography (eluted with 6:1 hexane:AcOEt)

Sources & evidence

ORD record
ord-a7dbd14a289b4b5d8269b55ce0110a9a
Source dataset
uspto-grants-2007_02
Patent number
US07173141B2

Reaction notes

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