HCID 15896052, compound → HCID 15896053, compound

HRID 1955078Notes

Reaction equation

HRID 1955078 reaction equation
C([O:8][NH:9][C:10](=[O:31])[CH2:11][N:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][NH:9][C:10](=[O:31])[CH2:11][N:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[S:13]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14]

Participants

4

Reactant 1

HCID 15896052HCID 15896052, compound

Product 1

HCID 15896053HCID 15896053, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-Benzyloxy-2-[octyl-(toluene-4-sulfonyl)amino]-acetamide (1.91 g, 0.0043 mol) was taken up in ethanol (150 ml), and 10% palladium on charcoal (800 mg) was added. Hydrogen gas was bubbled through the mixture for 2 hours at room temperature. The catalyst was removed by filtration and the solvent was removed under reduced pressure to give a crude solid which was purified by recrystallization from ethyl acetate/hexane (940 mg, 61%). m.p. 89° C.; 1H-NMR; δ(CDCl3), 7.69 (2H, d, J=8.2 Hz), 7.32 (2H, d, J=8.2 Hz), 3.76 (2H, s), 3.15 (1H, d, J=7.6 Hz), 3.12 (1H, d, J=7.9 Hz), 2.43 (3H, s), 1.58-1.41 (2H, m), 1.35-1.15 (10H, m) and 0.86 (3H, t, J=6.4 Hz). 13C-NMR; δ(CDCl3), 166.6, 144.2, 134.6, 129.9, 127.4, 50.7, 49.9, 31.6, 29.1, 29.0, 27.9, 26.6, 22.6, 21.5 and 14.0; IR (CDCl3), νmax 3413, 2929, 2858, 1682, 1467, 1401, 1346, 1162 and 1091 cm-1. Found: C, 57.27; H, 7.87; N, 7.95%; C17H28N2O4S requires C, 57.28; H, 7.92; N, 7.86%.

Workup

  1. customHydrogen gas was bubbled through the mixture for 2 hours at room temperature
  2. customThe catalyst was removed by filtration
  3. customthe solvent was removed under reduced pressure
  4. customto give a crude solid which
  5. customwas purified by recrystallization from ethyl acetate/hexane (940 mg, 61%)

Sources & evidence

ORD record
ord-8f199c39d2604c21bfde8bc9cdd45834
Source dataset
uspto-grants-2000_09
Patent number
US06124329

Reaction notes

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