Hydrochloric Acid → HCID 68689953, compound

HRID 2235042Notes

Reaction equation

HRID 2235042 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl.[C:31](OCC)(=[O:33])C>O1CCCC1.C(OCC)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:10](=[O:19])[CH2:11][CH2:12][CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:31]1[OH:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 60001153HCID 60001153, compound

Product 1

HCID 68689953HCID 68689953, compound

Reagents, catalysts & solvents 2

HCID 8025Ethyl formateSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of nitrogen, to a solution of ethyl 5-[(2,6-dichlorophenyl)amino]-5-oxopentanoate (9.22 g, the compound described in Reference Example 1 of WO03/043988) in tetrahydrofuran (150 mL) were added a solution of lithium bis(trimethylsilyl)amide (1.6 mol/L) in tetrahydrofuran (56.8 mL) and ethyl formate (4.90 mL) at −78° C. and the mixture was stirred on ice bath for 2 hours and then at room temperature for 4 days. The reaction mixture was added by hydrochloric acid (1 mol/L) and ethyl acetate on ice bath, then the water layer was extracted with ethyl acetate. The obtained extract was dried with anhydrous sodium sulfate, filtrated and concentrated to give the title compound. The obtained compound was used in the following reaction without further purification.

Workup

  1. waitat room temperature for 4 days
  2. extractionthe water layer was extracted with ethyl acetate
  3. extractionThe obtained extract
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57656f727a8a4d58a33e775591392526
Source dataset
uspto-grants-2010_05
Patent number
US07713998B2

Reaction notes

Loading…