Sodium Bicarbonate → HCID 58696361, compound

HRID 1178327Notes

Reaction equation

HRID 1178327 reaction equation
[C:1](=[O:4])(O)[O-:2].[Na+].[C:6]1([CH3:33])[CH:11]=CC(C([C@](C(O)=O)(O)[C@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=C[CH:7]=1.[Cl:34][C:35]1[CH:36]=[C:37]([C:42]([NH:48][CH3:49])([CH2:45][CH:46]=[CH2:47])[CH2:43][OH:44])[CH:38]=[CH:39][C:40]=1[Cl:41]>C(OCC)(=O)C>[C:6]([O:2][C:1](=[O:4])[N:48]([C:42]([C:37]1[CH:38]=[CH:39][C:40]([Cl:41])=[C:35]([Cl:34])[CH:36]=1)([CH2:43][OH:44])[CH2:45][CH:46]=[CH2:47])[CH3:49])([CH3:33])([CH3:11])[CH3:7]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 131726620HCID 131726620, compound

Product 1

HCID 58696361HCID 58696361, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (650 mL) were added to 2-(3,4-dichlorophenyl)-2-methylamino-4-pentenol (+)-di-p-toluoyl-D-tartrate (84.8 g). The insoluble matter was passed through Celite, followed by washing with ethyl acetate. The filtrate was partitioned. The ethyl acetate layer was washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane (250 mL). Di-tert-butoxydicarbonate (30.5 g) was added to the resultant solution, followed by stirring at 100° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue was purified through silica gel column chromatography (n-hexan:ethyl acetate=8:1 to 3:1), to thereby give the title compound (45.3 g, 99%).

Workup

  1. washby washing with ethyl acetate
  2. customThe filtrate was partitioned
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 1,4-dioxane (250 mL)
  7. additionDi-tert-butoxydicarbonate (30.5 g) was added to the resultant solution
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customthe residue was purified through silica gel column chromatography (n-hexan:ethyl acetate=8:1 to 3:1)

Sources & evidence

ORD record
ord-df6c9faa86b7466e82ee4c4f074dff15
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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