Dichloromethane → HCID 54547617, compound

HRID 2288769Notes

Reaction equation

HRID 2288769 reaction equation
C([N:11]1[CH2:18][C@@H:17]2[C@@H:13]([CH2:14][N:15]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]4=[O:35])=[CH:21][C:20]=3[F:36])[CH2:16]2)[CH2:12]1)(OCC1C=CC=CC=1)=O.C(Cl)Cl>[Pd].CO>[C@@H:17]12[CH2:16][N:15]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]4=[O:35])=[CH:21][C:20]=3[F:36])[CH2:14][C@@H:13]1[CH2:12][NH:11][CH2:18]2

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 54029891HCID 54029891, compound

Product 1

HCID 54547617HCID 54547617, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-N-[[3-[4-[cis-3-(Carbobenzyloxy)-3,7-diazabicyclo[3.3.0]octan-7-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (150 mg, 0.30 mmol), methylene chloride (5 mL), and methanol (10 mL) are combined with 10% palladium on carbon (30 mg) and placed under a hydrogen atmosphere (balloon) for 15 hours. The reaction is filtered through celite and concentrated in vacuo to give crude (S)-N-[[3-[4-[cis- 3,7-diazabicyclo[3.3.0]octan-7-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide. To the crude (S)-N-[[3-[4-[cis-3,7-diazabicyclo[3.3.0]octan-7-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (115 mg, 0.30 mmol) dissolved in pyridine (5 mL) at 0° C. is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (70 mg, 0.35 mmol), 4-dimethylaminopyridine (5 mg, 0.05 mmol), and isoxazole-5-carboxylic acid (40 mg, 0.35 mmol). The reaction is warmed to ambient temperature, stirred 15 hours, diluted with methylene chloride (30 mL). The organic phase is washed with 1N HCl (20 mL) and saline (20 mL), dried over sodium sulfate, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (97/3). The appropriate fractions are combined (Rf =0.16, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound, mp 172-175° C.

Workup

  1. customfor 15 hours
  2. filtrationThe reaction is filtered through celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-107c4cc9772644c98008aabfee406616
Source dataset
uspto-grants-2000_07
Patent number
US06090820

Reaction notes

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