HCID 10440854, compound → HCID 15816444, compound

HRID 2396611Notes

Reaction equation

HRID 2396611 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]([O:60]CC1C=CC=CC=1)[C:15](=[O:59])[CH2:16][CH2:17][C:18](=[O:58])[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([O:50]CC1C=CC=CC=1)[C:26](=[O:49])[CH2:27][CH2:28][C:29](=[O:48])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:36]([O:40]CC1C=CC=CC=1)[C:37](=[O:39])[CH3:38])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]([OH:60])[C:15](=[O:59])[CH2:16][CH2:17][C:18](=[O:58])[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]([OH:50])[C:26](=[O:49])[CH2:27][CH2:28][C:29](=[O:48])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:36]([OH:40])[C:37](=[O:39])[CH3:38])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 10440854HCID 10440854, compound

Product 1

HCID 15816444HCID 15816444, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd-C (227 mg) was added to a solution of (12) (0.346 g, 0.372 mmol) in MeOH (100 mL). The reaction flask was degassed three times with nitrogen and hydrogen gas was introduced at 1 atm. The mixture was rapidly stirred at room temperature for 20 minutes. After the reaction flask was evacuated and filled with nitrogen several times, the catalyst was filtered through a sintered glass filter (10-15μ) and solids were washed with MeOH. After solvent removal by rotary evaporation, the residue was passed through a short Sephadex LH-20 column, eluting with MeOH. The band was dried to provide 199 mg (81%) of (13) as an amorphous white solid: 300 MHz NMR (d6 -DMSO) δ 1.12-1.53 (m+s, 27 H), 1.95 (s, 3 H), 2.25 (t, 4 H, J=7), 2.52-2.60 (m, 4 H), 2.82-3.03 (m, 6 H), 3.43 (t, 6 H, J=6), 7.4 (m, 1 H), 7.8 (m, 2 H), 9.7 (br s, 3 H). The spectrum was identical to an authentic sample of (13).

Workup

  1. customThe reaction flask was degassed three times with nitrogen and hydrogen gas
  2. additionwas introduced at 1 atm
  3. customAfter the reaction flask was evacuated
  4. additionfilled with nitrogen several times
  5. filtrationthe catalyst was filtered through a sintered glass
  6. filtrationfilter (10-15μ) and solids
  7. washwere washed with MeOH
  8. customAfter solvent removal
  9. customby rotary evaporation
  10. washeluting with MeOH
  11. customThe band was dried

Sources & evidence

ORD record
ord-7cfd5fec1e4e46808ceb71e86ca3ad8b
Source dataset
uspto-grants-1996_02
Patent number
US05493053

Reaction notes

Loading…