Diisopropylamine → HCID 19594770, compound

HRID 612599Notes

Reaction equation

HRID 612599 reaction equation
[Li+].[CH3:2][CH:3]([N-]C(C)C)[CH3:4].[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].C(NC(C)C)(C)C.C(N(CC)[C:24]([C:26]1[C:27]([C:34]2[CH:39]=CC=CC=2OC(C)C)=[C:28]([O:32][CH3:33])[CH:29]=[CH:30][CH:31]=1)=[O:25])C.[O:46]1CCCC1>>[CH:3]([O:46][C:12]1[C:34]2[C:27]3[C:26](=[CH:31][CH:30]=[CH:29][C:28]=3[O:32][CH3:33])[C:24](=[O:25])[C:39]=2[CH:9]=[CH:10][CH:11]=1)([CH3:4])[CH3:2]

Participants

6

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 19594847HCID 19594847, compoundHCID 178418339Butyllithium

Product 1

HCID 19594770HCID 19594770, compoundYield 31%

Conditions

Temperature
0 °C

Procedure

Prepare LDA reagent by combining 4.1 mL n-butyl lithium (2.5 M in hexane) and 1.4 mL diisopropylamine dropwise, under argon in 40 mL tetrahydrofuran (THF) at -50° C. Allow the reaction to warm to 0° C. and dropwise add N,N-diethyl-2'-isopropoxy-6-methoxy-biphenyl-2-carboxamide (1.4 g, 4.1 mmole) dissolved in THF (15 mL) while stirring. Maintain the temperature at 0° C. for 10 minutes, then allow the reaction to obtain room temperature, as the color slowly changes to yellow. Heat the reaction at reflux for about 2 hours and observe the yellow solution darken. Quench the reaction with saturated ammonium chloride, extract with ether and wash the organic layer with water. Recrystalize from ether/methanol to obtain an orange solid of the title compound (0.34 g, 1.3 mmole, 31%). m.p. 118-120° C.

Workup

  1. customat -50° C
  2. customthe reaction
  3. temperatureMaintain the temperature at 0° C. for 10 minutes
  4. customthe reaction
  5. customto obtain room temperature, as the color
  6. temperatureHeat
  7. customthe reaction
  8. temperatureat reflux for about 2 hours
  9. customQuench
  10. customthe reaction with saturated ammonium chloride
  11. extractionextract with ether
  12. washwash the organic layer with water
  13. customRecrystalize from ether/methanol

Sources & evidence

ORD record
ord-f1cef425e67a4717b79e293520a37df7
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

Loading…