Sodium Bicarbonate → HCID 69885950, compound

HRID 2121900Notes

Reaction equation

HRID 2121900 reaction equation
C([O:5][C:6](=O)[CH2:7][O:8][C@H:9]1[CH2:32][O:31][C:12]2=[CH:13][CH:14]=[C:15]3[C:19]([N:18]([CH2:20][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH3:22])[N:17]=[CH:16]3)=[C:11]2[CH2:10]1)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>C1COCC1>[C:27]([Si:24]([CH3:26])([CH3:25])[O:23][C@H:21]([CH3:22])[CH2:20][N:18]1[C:19]2[C:15](=[CH:14][CH:13]=[C:12]3[O:31][CH2:32][C@H:9]([O:8][CH2:7][CH2:6][OH:5])[CH2:10][C:11]3=2)[CH:16]=[N:17]1)([CH3:29])([CH3:30])[CH3:28]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 69884487HCID 69884487, compound

Product 1

HCID 69885950HCID 69885950, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of the product from Example 13, Step A (1.76 g, 3.70 mmol) in anhydrous THF (30 mL) under nitrogen was added an 1 M solution of lithium aluminum hydride in THF (3.70 mL, 3.70 mmol). The reaction mixture was stirred for 0.5 h, cooled on ice, and a saturated aqueous solution of sodium bicarbonate (100 mL) was added. This mixture was extracted with ethyl acetate and the extract evaporated to an oil which was purified by chromatography (silica, gradient, 10% to 40% ethyl acetate in hexane) to give an oil (1.40 g, 93%): LCMS (+APCI) m/z 407 (M+H).

Workup

  1. temperaturecooled on ice
  2. extractionThis mixture was extracted with ethyl acetate
  3. customthe extract evaporated to an oil which
  4. customwas purified by chromatography (silica, gradient, 10% to 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f75d008a737f41119445a0de7210a837
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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