Sodium Carbonate → HCID 21308235, compound

HRID 1418663Notes

Reaction equation

HRID 1418663 reaction equation
[Si]([O:8][C:9]1([CH3:31])[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])=[CH:15][C:14]=2[F:30])[CH2:10]1)(C(C)(C)C)(C)C.F.C(=O)([O-])[O-].[Na+].[Na+].O1CCNC1=O>C(#N)C.ClCCl.CO.C(Cl)(Cl)Cl>[F:30][C:14]1[CH:15]=[C:16]([N:19]2[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]2=[O:29])[CH:17]=[CH:18][C:13]=1[N:11]1[CH2:10][C:9]([OH:8])([CH3:31])[CH2:12]1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 14917Hydrofluoric AcidHCID 739492-OxazolidinoneHCID 70197353HCID 70197353, compoundHCID 178435178HCID 178435178, compound

Product 1

HCID 21308235HCID 21308235, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

A solution of (S)-N-[[3-[4-[3-[(tert-butyldimethylsilyl)oxy]-3-methyl-1-azetidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (0.550 g, 1.22 mmol) in acetonitrile (20 mL) in a polypropylene bottle was treated with 40% aqueous hydrofluoric acid (5 mL) at ambient temperature. After 16 h TLC analysis (5% methanol/chloroform) revealed the deprotection was essentially complete. The reaction mixture was transferred to an erlenmeyer flask along with some dichloromethane (150 mL). The stirred mixture was carefully treated with saturated aqueous sodium carbonate (300 mL, gas evolution). After gas evolution ceased, the mixture was transferred to a separatory funnel and the phases separated. The aqueous phase was neutralized to pH 7 by the addition of 6N hydrochloric acid and extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. Radial chromatography over silica gel, eluting with 5% methanol/chloroform, afforded, after concentration of appropriate fractions, 0.374 g (91%) of the title oxazolidinone antibacterial agent as a white solid with mp 152°-153° C. and MS(EI) 337 (M+).

Workup

  1. customthe mixture was transferred to a separatory funnel
  2. customthe phases separated
  3. additionThe aqueous phase was neutralized to pH 7 by the addition of 6N hydrochloric acid
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washRadial chromatography over silica gel, eluting with 5% methanol/chloroform
  9. customafforded

Sources & evidence

ORD record
ord-52536298ccd24667bb51d7ffc1184ff6
Source dataset
uspto-grants-1999_03
Patent number
US05883093

Reaction notes

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