Dimethylformamide → HCID 18957361, compound

HRID 2379555Notes

Reaction equation

HRID 2379555 reaction equation
[H-].[Na+].CN(C=O)C.[C:8]1([C:14]2[N:15]=[C:16]([CH:25]3[NH:29][C:28](=[O:30])[CH2:27][CH2:26]3)[O:17][C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40]>Cl>[C:8]1([C:14]2[N:15]=[C:16]([CH:25]3[CH2:26][CH2:27][C:28](=[O:30])[N:29]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])[O:17][C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 11107373Methyl 8-bromooctanoateHCID 18367272HCID 18367272, compound

Product 1

HCID 18957361HCID 18957361, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

NaH (820 mg of a 50% dispersion, 17 mmol) was covered with DMF (80 mL) and 5-(4,5-diphenyl-2-oxazolyl)-2-pyrrolidinone (4.00 g, 13 mmol) added. The mixture was stirred at about 120° C. for about 15 minutes, cooled to room temperature and methyl 8-bromooctanoate (3.42 g, 14.5 mmol) added. The mixture was heated at about 110° C. for about 1 hour, cooled, diluted with 1N HCl and extracted with Et2O (3 times). The combined extracts were washed with H2O (3 times), dried over Na2SO4 and the solvent evaporated. The residual oil was chromatographed on a column of silica gel using Et2O as eluent to afford methyl 2-(4,5-Diphenyl-2-oxazolyl)-5-oxo-l-pyrrolidineoctanoate (4.85 g, 80%) as an oil. IR (Film) 1740 (CO2CH3), 1695 (N.CO) cm-1 ; 1H NMR (CDCl3) δ1.18-1.60 (10H, m, CH2), 2.20 (2H, t, J=7 Hz, CH2CO2CH3), 2.30-2.55 (3H, m, CH2 of ring), 2.73 (1H, m, CH2 of ring), 3.00 (2H, m, NCH2 of side chain), 3.61 (3H, s, CO2CH3), 4.86 (1H, m, CHN of ring), 7.25-7.40 (6H, m, aromatic H) , 7.50-7.70 (4H, m, aromatic H), MS m/z 461 (MH+).

Workup

  1. additionadded
  2. temperaturecooled to room temperature
  3. temperatureThe mixture was heated at about 110° C. for about 1 hour
  4. temperaturecooled
  5. extractionextracted with Et2O (3 times)
  6. washThe combined extracts were washed with H2O (3 times)
  7. dry with materialdried over Na2SO4
  8. customthe solvent evaporated
  9. customThe residual oil was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-4fe82b56f1054062974821c991cafafc
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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