Sodium Hydroxide → HCID 86726819, compound

HRID 1499602Notes

Reaction equation

HRID 1499602 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:42])[C@H:15]([CH:39]1[CH2:41][CH2:40]1)[C@H:16]([C@H:25]1[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[N:26]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])C1C=CC=CC=1.[BH4-].[Li+].[OH-].[Na+]>C1COCC1.CCO.C(OCC)C>[Si:18]([O:17][C@@H:16]([C@H:25]1[CH2:29][O:28][C:27]([CH3:30])([CH3:31])[N:26]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:15]([CH:39]1[CH2:41][CH2:40]1)[CH2:14][OH:42])([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:20])[CH3:19]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 86726818HCID 86726818, compound

Product 1

HCID 86726819HCID 86726819, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl (4R)-4-((1R,2R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-1-{[tert-butyl(dimethyl)silyl]oxy}-2-cyclopropyl-3-oxopropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (3.3 g, 5.5 mmol) in anhydrous THF (50 mL) and EtOH (1 mL) was cooled to −30° C. prior to the addition of lithium tetrahydroborate (0.24 g, 11 mmol) under an atmosphere of nitrogen. The reaction mixture was allowed to gradually warm to ambient temperature while stirring for 20 h. The crude reaction mixture was diluted with diethyl ether (36 mL) and cooled to 0° C. prior to the addition of 1 M NaOH (aq.) (36 mL). Upon separation of the layers that resulted, the aqueous layer was extracted with EtOAc several times and the combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography (120 g silica gel, eluting with 0-40% EtOAc/hexanes) to afford the sub-title compound (1.27 g, 54%). LC/MS (ESI) m/z calc. for C22H43NO5SiNa: 452.3 [M+Na]+. found 452.0.

Workup

  1. customThe crude reaction mixture
  2. temperaturecooled to 0° C.
  3. customUpon separation of the layers that
  4. customresulted
  5. extractionthe aqueous layer was extracted with EtOAc several times
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by flash column chromatography (120 g silica gel, eluting with 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d1d7c8eee3fd40b5a696cf21ee5c7d90
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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