Hydrochloric Acid → HCID 19022161, compound

HRID 1109369Notes

Reaction equation

HRID 1109369 reaction equation
[Si]([O:8][N:9]([CH3:18])[C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17])=[O:11])(C(C)(C)C)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[O:30][C:31](=O)[C:32]1[CH:37]=[C:36]([C:38]([CH3:41])([CH3:40])[CH3:39])[C:35]([O:42]COC)=[C:34]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:33]=1.Cl>C1COCC1.CC(C)=O.C(OCC)(=O)C>[OH:8][N:9]([CH3:18])[C:10]([N:12]1[CH2:16][CH2:15][CH:14]([C:31](=[O:30])[C:32]2[CH:37]=[C:36]([C:38]([CH3:39])([CH3:40])[CH3:41])[C:35]([OH:42])=[C:34]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:33]=2)[C:13]1=[O:17])=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 19022128HCID 19022128, compoundHCID 19022177HCID 19022177, compound

Product 1

HCID 19022161HCID 19022161, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a chilled solution (-78° C.) of 2 g (7.34 mmol) of the thus obtained 1-(N-tert-butyldimethylsilyloxy-N-methylcarbamoyl)pyrrolidin-2-one in THF (5 ml) was added 8.1 ml (8.1 mmol) of a THF solution of 1.0M lithium bis(trimethylsilyl)amide under a nitrogen atmosphere, and the mixture was stirred for 1 hour. To the reaction mixture was dropwise added 5 ml of a THF solution of 1.55 g (5 mmol) of methyl-3,5-di-tert-butyl-4-methoxymethyloxybenzoate while being stirred at room temperature for 20 hours. The reaction mixture was poured into ethyl acetate, washed with 0.1N hydrochloric acid and saturated brine, dried over magnesium sulfate and evaporated to give a residue, which was dissolved in 12 ml of acetone and added with 0.6 ml of conc. hydrochloric acid. The reaction mixture was stirred at room temperature for 20 hours, and poured into ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate and evaporated to give a residue, which was chromatographed on silica gel (toluene/ethyl acetate=10/1) to give 200 mg of the objective compound (Ia-20) as white amorphous in 10% yield.

Workup

  1. stirringwhile being stirred at room temperature for 20 hours
  2. washwashed with 0.1N hydrochloric acid and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a residue, which
  6. stirringThe reaction mixture was stirred at room temperature for 20 hours
  7. washwashed with water and saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customto give a residue, which
  11. customwas chromatographed on silica gel (toluene/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-80b82019a77f40d694cfeabced47f86d
Source dataset
uspto-grants-1994_06
Patent number
US05319099

Reaction notes

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