Sulfuric Acid → HCID 67148302, compound

HRID 2428123Notes

Reaction equation

HRID 2428123 reaction equation
[OH:1]S(O)(=O)=O.[C:6]([O:10][C:11](=[O:27])[N:12]([CH2:16][C:17]1[CH:22]=[C:21]([CH2:23][CH2:24][OH:25])[CH:20]=[CH:19][C:18]=1[Cl:26])[CH:13]1[CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7]>O.CC(C)=O>[C:6]([O:10][C:11]([N:12]([CH2:16][C:17]1[CH:22]=[C:21]([CH2:23][C:24]([OH:1])=[O:25])[CH:20]=[CH:19][C:18]=1[Cl:26])[CH:13]1[CH2:14][CH2:15]1)=[O:27])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 67148838HCID 67148838, compound

Product 1

HCID 67148302HCID 67148302, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Conc. H2SO4 (98%, 5.80 mL) was carefully added to a suspension of CrO3 (6.70 g, 67.0 mmol) in water (12.5 mL). Water was slowly added up to a total volume of 22.5 mL, at which stage the mixture was a clear sol. This sol. was added dropwise to a sol. of [2-chloro-5-(2-hydroxy-ethyl)-benzyl]-cyclopropyl-carbamic acid tert-butyl ester (13.0 g, 39.9 mmol) in acetone (140 mL) at 0° C. When the addition was complete, the mixture was stirred at 0° C. for 30 min. The mixture was filtered, and the filtrate was evaporated under reduced pressure. The residue was diluted with EtOAc, and the resulting mixture was washed with aq. 1M HCl. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (12.2 g, 90%) that was used further without purification. LC-MS: tR=0.95 min; ES+: 325.35.

Workup

  1. additionWhen the addition
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. additionThe residue was diluted with EtOAc
  5. washthe resulting mixture was washed with aq. 1M HCl
  6. dry with materiallayer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-913ea8e237c44d5abbdfd33c046a8618
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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