Hydrochloric Acid → HCID 118151892, compound

HRID 1506993Notes

Reaction equation

HRID 1506993 reaction equation
[S:1](=[O:22])(=[O:21])([O:3][CH2:4][C@@H:5]1[C@@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[O:8][C:7](C)(C)[O:6]1)[NH2:2].Cl.C1N=CN(C(N2C=NC=C2)=[O:30])C=1>CCOC(C)=O>[S:1](=[O:22])(=[O:21])([O:3][CH2:4][C@@H:5]1[C@@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[O:8][C:7](=[O:30])[O:6]1)[NH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 118151776HCID 118151776, compound

Product 1

HCID 118151892HCID 118151892, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To a stirred solution of ((4R,5R)-5-(2-nitrophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate (Example 77, 5.2 g, 16 mmol) in EtOAc (50 mL) was added 3N HCl (24.6 mL, 80.0 mmol) at room temperature. The mixture was stirred for 5 h. The resulting mixture was diluted with EtOAc, washed with sat. NaHCO3, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product stirred in THF (35 mL) was added CDI (2.91 g, 17.9 mmol) at room temperature. The mixture was stirred for 1 h. The resulting mixture was diluted with EtOAc, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 gel column chromatography to produce the title compound (2.6 g, 60˜80%)

Workup

  1. washwashed with sat. NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. stirringThe crude product stirred in THF (35 mL)
  6. stirringThe mixture was stirred for 1 h
  7. washwashed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by SiO2 gel column chromatography

Sources & evidence

ORD record
ord-f7c72363b687485f9d8974457010295a
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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