Sodium Hydroxide → HCID 18657619, compound

HRID 1492013Notes

Reaction equation

HRID 1492013 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]1[CH2:20][CH2:21][C:22]([O:24]C)=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[Si:1]([O:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]1[CH2:20][CH2:21][C:22]([OH:24])=[O:23])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57126774HCID 57126774, compound

Product 1

HCID 18657619HCID 18657619, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.82 g of methyl (2S,3S,4S)-3-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)-tetrahydrofuran-3-yl]propanoate in 25 ml of methanol is added 10 ml (0.01 mol) of 1N sodium hydroxide, the mixture is stirred at room temperature overnight, evaporated to a small volume and extracted with ethyl acetate. The aqueous layer is diluted with 20 ml of methylene chloride, the mixture is cooled to 0° C. and the pH of the aqueous layer is adjusted with stirring to 5.5 with 2N aqueous hydrochloric acid. The methylene chloride layer is dried (MgSO4) and evaporated. The residue is triturated with ethyl acetate to give (2S,3S,4S)-3-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]propanoic acid with mp 93°-94° C.

Workup

  1. customevaporated to a small volume
  2. extractionextracted with ethyl acetate
  3. additionThe aqueous layer is diluted with 20 ml of methylene chloride
  4. temperaturethe mixture is cooled to 0° C.
  5. stirringwith stirring to 5.5 with 2N aqueous hydrochloric acid
  6. dry with materialThe methylene chloride layer is dried (MgSO4)
  7. customevaporated
  8. customThe residue is triturated with ethyl acetate

Sources & evidence

ORD record
ord-0e8a342ae95248dca520776dc1903fda
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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