Hydrochloric Acid → HCID 21978383, compound

HRID 10213Notes

Reaction equation

HRID 10213 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([CH2:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])(=[O:15])=[O:14])[CH2:9]2)C=CC=CC=1.[H][H].[ClH:31]>C(O)C.O.[OH-].[OH-].[Pd+2]>[ClH:31].[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([CH2:12][CH:10]1[CH2:11][NH:8][CH2:9]1)(=[O:14])=[O:15]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 219783651-(Diphenylmethyl)-3-{[(2-fluorophenyl)sulfonyl]methyl}azetidineHCID 178418361HCID 178418361, compound

Product 1

HCID 21978383HCID 21978383, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(Diphenylmethyl)-3-{[(2-fluorophenyl)sulfonyl]methyl}azetidine (1.33 g, 3.37 mmol) was dissolved in ethanol (80 mL). The solution was diluted with 2M hydrochloric acid (1.8 mL) and water (20 mL). 20% Palladium hydroxide on carbon (0.63 g) was added and the mixture shaken on a Parr apparatus under 50 psi of hydrogen for 3.5 h. The catalyst was removed by filtration and the filtrate concentrated to a small volume. The solid present was redissolved by adding ethanol and the solution filtered. The filtrate was concentrated to a small volume once again to give a crystalline solid which was collected under suction, washed with cold ethanol and dried in vacuo to afford the title compound as colourless crystals (0.81 g, 91%); 1H NMR (500 MHz, CD3OD) δ 3.34–3.42 (1H, m), 3.80 (2H, d, J=7.6 Hz), 4.07 (2H, t, J=10 Hz), 4.14 (2H, t, J=10 Hz), 7.41–7.49 (2H, m), 7.80–7.84 (1H, m), 7.90–7.92 (1H, m); 19F NMR (471 MHz, CD3OD) δ −110.6; m/z (ES+) 230 ([M+H]+, 100%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated to a small volume
  3. dissolutionThe solid present was redissolved
  4. additionby adding ethanol
  5. filtrationthe solution filtered
  6. concentrationThe filtrate was concentrated to a small volume once again
  7. customto give a crystalline solid which
  8. customwas collected under suction
  9. washwashed with cold ethanol
  10. customdried in vacuo

Sources & evidence

ORD record
ord-f46740ff4a414e98a0bfaed86498a7e9
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

Loading…