Ammonium Chloride → HCID 67157096, compound

HRID 901768Notes

Reaction equation

HRID 901768 reaction equation
[C:1]([O:9][C@H:10]1[C@H:16]2[CH2:17][N:18]([C:19]([O:21][C:22](=O)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C@@H:11]1[C@H:12]([O:15]2)[O:13]C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>FC(F)(F)C(O)=O.O.O>[C:1]([O:9][C@H:10]1[C@H:16]([OH:15])[CH2:17][N:18]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[C@@H:11]1[CH2:12][OH:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 87455623HCID 87455623, compound

Product 1

HCID 67157096HCID 67157096, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

The compound (15.8 g, 41.3 mmol) synthesized in Example 1 (1g) was dissolved in trifluoroacetic acid:water (4:1, 160 mL) and the mixture was stirred at room temperature for 15 minutes. After water (200 mL) was added to the reaction mixture at 0° C. and the mixture was extracted with methylene chloride (300 mL), the organic layer was washed with saturated aqueous sodium hydrogencarbonate (200 mL) and saturated brine (200 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was dissolved in ethanol (150 mL) and the compound obtained by dissolving sodium borohydride (0.78 g, 20.7 mmol) in water (15 mL) was added thereto, followed by stirring of the mixture at 0° C. for 20 minutes. After saturated aqueous ammonium chloride (20 mL) was added to the reaction mixture at 0° C., ethanol was distilled off under reduced pressure. After water (100 mL) was added thereto and the mixture was extracted with ethyl acetate (100 mL), the organic layer was washed with saturated brine (100 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 1:1, V/V) to obtain the desired title compound (14.2 g, yield 89%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with methylene chloride (300 mL)
  2. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate (200 mL) and saturated brine (200 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationby distilling off of the solvent under reduced pressure
  5. dissolutionThe residue was dissolved in ethanol (150 mL)
  6. customthe compound obtained
  7. additionwas added
  8. stirringby stirring of the mixture at 0° C. for 20 minutes
  9. distillationethanol was distilled off under reduced pressure
  10. additionAfter water (100 mL) was added
  11. extractionthe mixture was extracted with ethyl acetate (100 mL)
  12. washthe organic layer was washed with saturated brine (100 mL)
  13. dry with materialdried with anhydrous sodium sulfate
  14. distillationby distilling off of the solvent under reduced pressure
  15. customThe residue was purified

Sources & evidence

ORD record
ord-8de7bb86d9a84d56a60f4d4788bf3003
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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