Diisopropylamine → HCID 11141969, compound

HRID 612612Notes

Reaction equation

HRID 612612 reaction equation
[Li+].CC([N-]C(C)C)C.C([Li])CCC.C(NC(C)C)(C)C.C(N(CC)[C:24]([C:26]1[C:27]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][CH3:45])=[CH:38][C:37]=2[O:46][CH3:47])=[C:28]([O:32][CH:33]([CH3:35])[CH3:34])[CH:29]=[CH:30][CH:31]=1)=[O:25])C>C1COCC1>[CH:33]([O:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]2[C:27]=1[C:36]1[C:37]([O:46][CH3:47])=[CH:38][C:39]([O:42][CH2:43][CH2:44][CH3:45])=[CH:40][C:41]=1[C:24]2=[O:25])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 19594641HCID 19594641, compoundHCID 178418339Butyllithium

Product 1

HCID 11141969HCID 11141969, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prepare LDA reagent by reacting n-butyl lithium and diisopropylamine as in Example 7C to obtain 0.05 mole in THF (50 mL) at 0° C. At 0° C., dropwise add N,N-diethyl-6-isopropyloxy-2'-methoxy-4'-propyloxy-biphenyl-2-carboxamide (4.3 g, 0.011 mole) in THF (20 mL). Warm the mixture to ambient temperature, stir for 1 hour then heat to reflux for 1.5 hours. Workup the mixture as in Example 7C and chromatograph eluting with 50%/50% EtOAc/hexane to give the title compound as a red solid (2.6 g, 63%). m.p. 114°-116° C.

Workup

  1. customAt 0° C.
  2. temperaturethen heat
  3. temperatureto reflux for 1.5 hours
  4. washWorkup the mixture as in Example 7C and chromatograph eluting with 50%/50% EtOAc/hexane

Sources & evidence

ORD record
ord-f837519f33ac4d5b968ee7143b63259c
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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