Dimethylformamide → HCID 178444001, compound

HRID 230384

Reaction equation

HRID 230384 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:10](O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=1)[C:29](=O)CBr.C([O-])(=O)C.[NH4+:40].C[N:42]([CH3:45])C=O>C(O)C.C(OCC)(=O)C.C1(C)C(C)=CC=CC=1.O>[Br:25][C:26]1[CH:27]=[C:28]([C:29]2[N:40]=[C:10]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[NH:42][CH:45]=2)[CH:33]=[CH:34][CH:35]=1

Participants

10

Reactant 5

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 517165Ammonium AcetateHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-oneHCID 536500462-(((Tert-butoxy)carbonyl)amino)-6-methylheptanoic acid

Product 1

HCID 178444001HCID 178444001, compoundYield 63%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
23 °C

Procedure

A mixture of 2-((tert-butoxycarbonyl)amino)-6-methylheptanoic acid (3.5 g; 0.0135 mol) and cesium carbonate (4.89 g; 0.015 mol) in 100 ml ethanol was agitated at about 23° C. for about 1 hour. The ethanol was eliminated by evaporation under reduced pressure in a rotative evaporator. The mixture obtained was dissolved in 100 ml of dimethylformamide and 3-bromophenacyl bromide (3.75 g; 0.0135 mol) was then added. After about 16 hours agitation, the solvent was evaporated under reduced pressure. The mixture obtained was taken up in ethyl acetate and the cesium bromide was then filtered. The ethyl acetate of the filtrate was evaporated and the reaction oil was taken up in a mixture of xylene (100 ml) and ammonium acetate (46.2 g; 0.6 mol). The mixture was then heated to reflux for about one hour and a half and, after cooling, a mixture of icy water and ethyl acetate was poured in the reaction medium. After phase separation, the organic phase was washed with a sodium saturated bicarbonate solution, dried over magnesium sulfate and then evaporated under vacuum. The solid obtained was filtered and then washed with ether to produce a white powder (yield of 63%). Melting point: 134-136° C. MH+=436.2.

Workup

  1. customThe ethanol was eliminated by evaporation under reduced pressure in a rotative evaporator
  2. customThe mixture obtained
  3. waitAfter about 16 hours agitation
  4. customthe solvent was evaporated under reduced pressure
  5. customThe mixture obtained
  6. filtrationthe cesium bromide was then filtered
  7. customThe ethyl acetate of the filtrate was evaporated
  8. customthe reaction oil
  9. temperatureThe mixture was then heated
  10. temperatureto reflux for about one hour
  11. temperaturea half and, after cooling
  12. additionwas poured in the reaction medium
  13. customAfter phase separation
  14. washthe organic phase was washed with a sodium saturated bicarbonate solution
  15. dry with materialdried over magnesium sulfate
  16. customevaporated under vacuum
  17. customThe solid obtained
  18. filtrationwas filtered
  19. washwashed with ether

Sources & evidence

ORD record
ord-bed07fd92cf8416a90801ca326e0ddad
Source dataset
uspto-grants-2009_07
Patent number
US07566734B2

Linked notes

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