O-Methylhydroxylamine hydrochloride → HCID 9881022, compound

HRID 1991235Notes

Reaction equation

HRID 1991235 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([C:19](O)=[O:20])[O:16][C:15]2=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.Cl.[CH3:24][O:25][NH2:26].Cl.CN(C)CCCN=C=NCC>O1CCCC1.O.O>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([C:19]([NH:26][O:25][CH3:24])=[O:20])[O:16][C:15]2=[O:22])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23730106HCID 23730106, compound

Product 1

HCID 9881022HCID 9881022, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid (EXAMPLE 1, Step 1, 150 mg, 0.483 mmol) and O-methylhydroxylamine hydrochloride (61 mg, 0.724 mmol) in tetrahydrofuran/water (1/1, 4.8 mL) is treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (278 mg, 1.45 mmol), and the resulting mixture is stirred at ambient temperature for 30 minutes and is then diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). The combined organic phase is washed with water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the crude product is chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with methanoumethylene chloride (2.5/97.5). Pooling and concentration of those fractions with an Rf=0.53 by TLC (methanol/chloroform, 10/90) gives the title compound, mp 206-208° C. (decomp.); MS (ESI+) for C15H18FN3O5 m/z 340 (M+H)+; [α]25D=−56° (c 0.92, DMSO).

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe combined organic phase is washed with water (10 mL) and saline (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe crude product is chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge
  6. washeluting with methanoumethylene chloride (2.5/97.5)

Sources & evidence

ORD record
ord-4d7ff55f849943b0ab5ff0ebb6410d21
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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