Hydrochloric Acid → HCID 15552091, compound

HRID 587053Notes

Reaction equation

[OH-].[Na+].[CH:3]([N:6]1C[CH2:9][CH2:8][C:7]1=O)([CH3:5])[CH3:4].Cl.[C:13](=[O:16])([O-])[O-:14].[Na+].[Na+].[Br:19][C:20]1[CH:21]=[CH:22][C:23](F)=[C:24]([CH:27]=1)[CH:25]=[O:26]>CS(C)=O>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([N:6]([CH:3]([CH3:5])[CH3:4])[CH2:7][CH2:8][CH2:9][C:13]([OH:14])=[O:16])=[C:24]([CH:25]=[O:26])[CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4N sodium hydroxide (36 ml) was added to 1-isopropyl-2-pyrrolidone (9.2 g), and the mixture was stirred for 3.5 hours. After cooled to 0° C., the mixture was neutralized with concentrated hydrochloric acid. After sodium carbonate (15.3 g) was added thereto, a solution of 5-bromo-2-fluorobenzaldehyde (7.3 g) in dimethyl sulfoxide (96 ml) was added thereto, and the mixture was heated to reflux for 5 hours. After cooled to room temperature, pH was adjusted to approximate 4 with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate/THF. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2) to give 4-(4-bromo-2-formylisopropylanilino)butyric acid (0.92 g).

Workup

temperaturethe mixture was heated
temperatureto reflux for 5 hours
temperatureAfter cooled to room temperature
extractionthe mixture was extracted with ethyl acetate/THF
washThe extract was washed with saturated brine
dry with materialdried with magnesium sulfate
customThe solvent was removed under reduced pressure
customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2)

Sources & evidence

ORD record: ord-e17d7eef7a4547969de5e0a5055c0b58
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936602B1

Reaction notes

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