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 1661431Notes

Reaction equation

HRID 1661431 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-4b8d3b8b94ff432299798de1f77722f0
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

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