Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-(2-{2-[3-(benzyloxy)butyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamide

HRID 1802730Notes

Reaction equation

HRID 1802730 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:18](=[O:31])[CH2:19][CH2:20][CH:21]([O:23]CC3C=CC=CC=3)[CH3:22])[C:14]=2O)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].[C:32]1([CH3:42])[CH:37]=[CH:36][C:35](S([O-])(=O)=O)=[CH:34][CH:33]=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[CH2:42]([O:23][CH:21]([CH3:22])[CH2:20][CH2:19][C:18]1[O:31][C:14]2[C:15]3[CH:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH2:8][CH2:9][C:10]=3[CH:11]=[CH:12][C:13]=2[N:17]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57781273N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-4-(benzyloxy)pentanamide

Product 1

HCID 57781203N-(2-{2-[3-(benzyloxy)butyl]-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl}ethyl)acetamideYield 402.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-4-(benzyloxy)pentanamide (210 mg, 0.495 mmol) and pyridinium p-toluenesulfonate (24.8 mg, 0.0991 mmol) were heated under reflux in xylene (10 mL) for 14 hr. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=30/70→60/40) to give the title compound (162 mg, yield 81%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=30/70→60/40)

Sources & evidence

ORD record
ord-d4ad57101d18439697287f3dd1b4e605
Source dataset
uspto-grants-2013_01
Patent number
US08349879B2

Reaction notes

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