Ammonium → HCID 57471474, compound

HRID 2177130Notes

Reaction equation

HRID 2177130 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH2:17][S:18]([CH2:21][CH2:22][CH3:23])(=O)=O)[CH:14]=2)[CH2:9][CH2:8][CH:7]1[NH:24][C:25](=[O:29])[O:26][CH2:27][CH3:28].[NH4+]>CO.[Pd]>[CH2:27]([O:26][C:25](=[O:29])[NH:24][CH:7]1[CH2:8][CH2:9][C:10]2[C:15](=[CH:14][C:13]([CH2:16][CH2:17][S:18][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=2)[CH:6]1[CH2:5][C:4]1[CH:3]=[CH:2][CH:32]=[CH:31][CH:30]=1)[CH3:28]

Participants

5

Reactant 2

HCID 223AmmoniumHCID 57471473HCID 57471473, compound

Product 1

HCID 57471474HCID 57471474, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 1-(3-chlorobenzyl)-7-(2-(propylsulfonyl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (27.1 mg, 0.057 mmol) and ammonium form late (71.5 mg, 1.134 mmol) were dissolved in 5 ml MeOH. Pd/C (0.845 mg, 7.94 μmol) was added and stirred at 80° C. for 4 h. The mixture was filtered, the solvent evaporated, the residue re-dissolved in ethyl acetate, which was subsequently washed with water, NaHCO3 and brine, dried, filtered. Solvent was evaporated to obtain white solid which was purified by chromatography affording 12.7 mg of product as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent evaporated
  3. dissolutionthe residue re-dissolved in ethyl acetate
  4. washwhich was subsequently washed with water, NaHCO3 and brine
  5. customdried
  6. filtrationfiltered
  7. customSolvent was evaporated
  8. customto obtain white solid which
  9. customwas purified by chromatography

Sources & evidence

ORD record
ord-fa90a9f0bb50422aba8d6aae6cd1fe2f
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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