Acetonitrile → HCID 70193791, compound

HRID 1418653Notes

Reaction equation

HRID 1418653 reaction equation
C(#N)C.[Si]([O:11][CH:12]1[CH2:15][N:14]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]3=[O:32])=[CH:18][C:17]=2[F:33])[CH2:13]1)(C(C)(C)C)(C)C.F.C(=O)(O)[O-].[Na+]>O>[F:33][C:17]1[CH:18]=[C:19]([N:22]2[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]2=[O:32])[CH:20]=[CH:21][C:16]=1[N:14]1[CH2:15][CH:12]([OH:11])[CH2:13]1

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 54073333HCID 54073333, compoundHCID 178435178HCID 178435178, compound

Product 1

HCID 70193791HCID 70193791, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An acetonitrile (55 mL) solution of (S)-N-[[3-[4-[3-[(tert-butyldimethylsilyl)oxy]-1-azetidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (1.23 g, 2.81 mmol) in a polypropylene bottle was treated with 38% aqueous hydrofluoric acid (15 mL) at ambient temperature. TLC analysis revealed the deprotection to be complete after 3 h. The reaction mixture was diluted with water (15 mL) and neutralized with solid sodium bicarbonate. Additional water was added (50 mL) and the mixture extracted with chloroform. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title oxazolidinone antibacterial agent as an off-white solid with mp 174°-177° C. and MS(EI) 323 (M+).

Workup

  1. extractionthe mixture extracted with chloroform
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea9dff9a26374972891aafce926e944d
Source dataset
uspto-grants-1999_03
Patent number
US05883093

Reaction notes

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