Hydrochloric Acid → HCID 86673328, compound

HRID 332623Notes

Reaction equation

HRID 332623 reaction equation
[Si:1]([O:8][C:9]1[S:13]C(C)=NC=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:20]CCCCC.[CH3:26][N:27]([CH3:30])C=O.Cl.[O:32]1CCC[CH2:33]1>O>[Si:1]([O:8][C:9]1[S:13][C:26]([CH:33]=[O:32])=[N:27][C:30]=1[CH3:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 70945116HCID 70945116, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 86673328HCID 86673328, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

The compound (4.5 g, 20 mmol) obtained in step 1 was dissolved in tetrahydrofuran (30 mL), and 2.5M n-butyllithium/hexane solution (16 mL, 40 mmol) was added dropwise at −78° C. The reaction mixture was stirred at −78° C. for 35 minutes, N,N-dimethylformamide (4 ml) was added dropwise, and the mixture was stirred at −30° C. for 1 hour. The reaction mixture was neutralized with water and 2N hydrochloric acid, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (1.6 g).

Workup

  1. stirringthe mixture was stirred at −30° C. for 1 hour
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c53da974e43d49faa3257a20a79bf668
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

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