Hydroxylamine → HCID 69744704, compound

HRID 2120077Notes

Reaction equation

HRID 2120077 reaction equation
[C:1]([C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9](Cl)=[C:10]([F:15])[CH:11]=2)[N:6]([CH:17]2[CH2:19][CH2:18]2)[CH:5]=1)([OH:3])=[O:2].N[OH:21].[C:22]([N:29]1[CH:33]=[CH:32]N=C1)(N1C=CN=C1)=[O:23].N1C=CN=C1.[CH3:39][N:40]1[C:44](=[O:45])[CH2:43]CC1>C1COCC1>[C:44]([NH:40][CH2:39][C@@H:32]1[O:21][C:22](=[O:23])[N:29]([C:9]2[CH:8]=[C:7]3[C:12]([C:13](=[O:14])[C:4]([C:1]([OH:3])=[O:2])=[CH:5][N:6]3[CH:17]3[CH2:19][CH2:18]3)=[CH:11][C:10]=2[F:15])[CH2:33]1)(=[O:45])[CH3:43]

Participants

7

Reactant 5

HCID 787HydroxylamineHCID 795ImidazoleHCID 13387N-methyl-2-pyrrolidoneHCID 682631,1'-CarbonyldiimidazoleHCID 483180Fluoroquinolonic acid

Product 1

HCID 69744704HCID 69744704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 19 is prepared according to the General Procedure Synthesis of Quinolone-7-yl Linked Oxazolidinones from 1-acetyl-3-amino-2-(S)-oxypropylamine (2 mmol) using 3-carboxy-1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydroquinoline-4-one (0.282 g, 1 mmol). The first reaction step is performed at 120-130° C. for 48 h. The mixture is cooled to room temperature (r.t.), and a majority of the solvent removed under vacuum. The resulting amino alcohol intermediate is purified by silica gel column chromatography (eluent: dichloromethane-MeOH). Cyclization is performed by dissolving the amino alcohol (1 mmol) in an aprotic organic solvent (e.g., THF or NMP) (2-5 mL), in the presence of carbonyldiimidazole (1.1 mmol) and adding imidazole (1.0 mmol). The mixture is stirred at 20-40° C. for 1-3 h. The solvent is removed under vacuum, and the product is purified by silica gel column chromatography (eluent: dichloromethane-MeOH).

Workup

  1. customaccording to the General Procedure Synthesis of Quinolone-7-yl
  2. customThe first reaction step
  3. customa majority of the solvent removed under vacuum
  4. customThe resulting amino alcohol intermediate is purified by silica gel column chromatography (eluent: dichloromethane-MeOH)
  5. customThe solvent is removed under vacuum
  6. customthe product is purified by silica gel column chromatography (eluent: dichloromethane-MeOH)

Sources & evidence

ORD record
ord-b77c96409bc342e3819193d07b026b4a
Source dataset
uspto-grants-2004_02
Patent number
US06689769B2

Reaction notes

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