HCID 22176549, compound → Propane-2-sulfonic acid [2-(2-fluoro-4-methoxyphenyl)-2-hydroxy-propyl]-amide

HRID 1797218Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]([OH:15])([CH3:14])[CH2:12][NH2:13].N1([O:25][S:26]([CH:29]([CH3:31])[CH3:30])(=O)=[O:27])C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[F:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]([OH:15])([CH3:14])[CH2:12][NH:13][S:26]([CH:29]([CH3:31])[CH3:30])(=[O:27])=[O:25]

Participants

Conditions

Temperature: 120 °C

Procedure

2-(2-Fluoro-4-methoxy-phenyl)-2-hydroxy-propylamine hydrochloride was converted to the free base by partitioning between ethyl acetate and 1 M NaOH. The amine (1.0 g, 5.02 mmol) was combined with propane-2-sulfonic acid benzotriazol-1-yl ester (1.3 g, 5.52 mmol) in DMF (25 mL) and heated at 120° C. for 2 hr. then cooled to room temperature. The reaction mixture was diluted with ethyl acetate and extracted with 1 M HCl. The organic layer was separated and washed with water and saturated NaCl, dried (MgSO4), filtered, and concentrated to a yellow oil which was used in the next step without purification.

Workup

customby partitioning between ethyl acetate and 1 M NaOH
temperaturethen cooled to room temperature
extractionextracted with 1 M HCl
customThe organic layer was separated
washwashed with water and saturated NaCl
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated to a yellow oil which
customwas used in the next step without purification

Sources & evidence

ORD record: ord-20c9ed76b0f547ca9fda0875fc304844
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034045B1

Reaction notes

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