Hydrochloric Acid → ethyl 2-[(2-{(4S)-4-[(1E)-4,4-dimethyl-3-oxo-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylate

HRID 1888296Notes

Reaction equation

HRID 1888296 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:18])([CH2:14][CH2:15][CH2:16][CH3:17])[C:5](=[O:13])[CH2:6]P(=O)(OC)OC.[CH:19]([C@H:21]1[CH2:25][O:24][C:23](=[O:26])[N:22]1[CH2:27][CH2:28][S:29][C:30]1[S:31][CH:32]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:34]=1)=O.Cl>O1CCCC1>[CH3:18][C:4]([CH3:3])([CH2:14][CH2:15][CH2:16][CH3:17])[C:5](=[O:13])/[CH:6]=[CH:19]/[C@H:21]1[CH2:25][O:24][C:23](=[O:26])[N:22]1[CH2:27][CH2:28][S:29][C:30]1[S:31][CH:32]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 13018035Dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonateHCID 86650055ethyl 2-({2-[(4R)-4-formyl-2-oxo-1,3-oxazolidin-3-yl]ethyl}thio)-1,3-thiazole-4-carboxylate

Product 1

HCID 66857555ethyl 2-[(2-{(4S)-4-[(1E)-4,4-dimethyl-3-oxo-1-octenyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)thio]-1,3-thiazole-4-carboxylateYield 45.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To sodium hydride (60.0% in oil) (49.0 mg) was added slowly a solution of dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate (332 mg) in anhydrous tetrahydrofuran (7.30 mL) at 0° C. and the solution was stirred at room temperature for 1 hour. To the reaction solution was added slowly a solution of the compound 5 (336 mg) in anhydrous tetrahydrofuran (2.90 mL) at room temperature and the solution was stirred for 2 hours. To the reaction solution was added 1N hydrochloric acid at 0° C. and the solution was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2), to give the title compound (211 mg) having the following physical data.

Workup

  1. stirringthe solution was stirred for 2 hours
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-465e5ca765fc40f29e5b8e15a498322c
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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