Hydrochloric Acid → HCID 54463452, compound

HRID 1108555Notes

Reaction equation

HRID 1108555 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:15]2[CH2:19][CH:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([CH:13]=O)=[CH:9]1.[NH2:25][OH:26].[OH-].[Na+].Cl>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:15]2[CH2:19][CH:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([CH:13]=[N:25][OH:26])=[CH:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 9905524HCID 9905524, compound

Product 1

HCID 54463452HCID 54463452, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(-)-5-Acetamidomethyl-3-(3-fluoro-4-(3-formylpyrrol-1-yl)phenyl)isoxazoline (Example 15) (329 mg) is suspended in 4 ml 95% ethanol in a 50 ml one neck round bottom flask under nitrogen. The suspension is treated with hydroxylamine (80 mg) followed by sodium hydroxide (60 mg) and 0.4 ml water. The reaction is stirred 1 hour at room temperature, the pH is adjusted to 7 with 5% hydrochloric acid, and the white solid is collected. The solid is collected, washed with water, and is dried to give 300 mg (87%) of the title compound as a white solid. The title compound is obtained via chromatography over silica gel (230-400 mesh), eluting with 5% methanol/dichloromethane, mp 216-217° C., [α]25D -67° (c 0.67, DMSO).

Workup

  1. customthe white solid is collected
  2. customThe solid is collected
  3. washwashed with water
  4. customis dried

Sources & evidence

ORD record
ord-21044b00b2b141759500985d58573aae
Source dataset
uspto-grants-2000_05
Patent number
US06069141

Reaction notes

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