Sodium Bicarbonate → HCID 68768429, compound

HRID 1888307Notes

Reaction equation

HRID 1888307 reaction equation
[CH3:1][C:2]([O:24][Si:25]([CH3:28])([CH3:27])[CH3:26])([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:3][CH2:4]S(C1N(C2C=CC=CC=2)N=NN=1)(=O)=O.C[Si](C)(C)[N-][Si](C)(C)C.[K+].[CH:39]([C@H:41]1[C@H:45]([CH3:46])[O:44][C:43](=[O:47])[N:42]1[CH2:48][CH2:49][S:50][C:51]1[S:52][CH:53]=[C:54]([C:56]([O:58][CH2:59][CH2:60][CH2:61][CH3:62])=[O:57])[N:55]=1)=O.C(=O)(O)[O-].[Na+]>C(COC)OC>[CH3:46][C@@H:45]1[O:44][C:43](=[O:47])[N:42]([CH2:48][CH2:49][S:50][C:51]2[S:52][CH:53]=[C:54]([C:56]([O:58][CH2:59][CH2:60][CH2:61][CH3:62])=[O:57])[N:55]=2)[C@H:41]1/[CH:39]=[CH:4]/[CH2:3][C:2]([CH3:1])([O:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 23148108HCID 23148108, compoundHCID 86650059HCID 86650059, compound

Product 1

HCID 68768429HCID 68768429, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of the compound 41 (10.1 g) in dimethoxyethane (79 mL) was slowly added dropwise potassium hexamethyldisilazide (0.5M in toluene, 47.5 mL) at −78° C. and the solution was stirred at −78° C. for 54 minutes. To the reaction solution was slowly added dropwise a solution of the compound 42 (9.84 g) in dimethoxyethane (79 mL) and the solution was stirred at −78° C. for 25 minutes. The solution temperature was risen to 0° C. and the solution was stirred for 50 minutes. To the reaction solution was added an aqueous saturated sodium bicarbonate solution and the solution was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, and dried over anhydrous magnesium sulfate. The reaction solution was filtrated through Celite (Brand name) and concentrated. The obtained residue was purified by Yamazen Parallel Prep (Brand name; column: 3 L, inject column: 2 L, n-hexane:ethyl acetate=84:16) to give the title compound (6.62 g) having the following physical data.

Workup

  1. stirringthe solution was stirred at −78° C. for 25 minutes
  2. customwas risen to 0° C.
  3. stirringthe solution was stirred for 50 minutes
  4. extractionthe solution was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe reaction solution was filtrated through Celite (Brand name)
  8. concentrationconcentrated
  9. customThe obtained residue was purified by Yamazen Parallel Prep (Brand name; column: 3 L, inject column: 2 L, n-hexane:ethyl acetate=84:16)

Sources & evidence

ORD record
ord-a6193d45462a49768f134ee6a09a4f6c
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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