Acetone → HCID 11502536, compound

HRID 910031Notes

Reaction equation

HRID 910031 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)=[O:9])[CH:7]=1.[C:22]([O-:25])([O-])=[O:23].[K+].[K+].[CH3:28][C:29](C)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][C@@H:28]([CH3:29])[C:22]([OH:25])=[O:23])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)=[O:9])[CH:7]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 688693(5-Bromo-2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone

Product 1

HCID 11502536HCID 11502536, compoundYield 46%

Procedure

(5-Bromo-2-hydroxyphenyl)-(1-phenyl-1H-pyrazol-4-yl)ketone (100 mg, 0.29 mmol), (R)-(+)-bromoacetic acid (44 mg, 0.29 mmol) ethyl 2-bromopropionate and K2CO3 (80 mg, 0.58 mmol) in acetone was stirred at room temperature for 16 h. The reaction mixture was concentrated and the residue was partitioned between EtOAc and dilute HCl (pH˜1). The organic phase was dried (Na2SO4) and concentrated, and the residue was purified by flash chromatography (EtOAc:heptane, 1:1) to yield 55 mg (46%) of the title compound: Chiral HPLC (Column: Ciracel OD (0.46 cm×24 cm); Eluent: isocratic, 85% hexane+15% 2-propanol+0.1% TFA; Flow 0.5 mL/min) Rt 15.7 min, >90% e.e. (Racemic material eluates with baseline separation of enantiomers: Rt 15.7 and 16.7 min.) MS and NMR spectra correspond to racemic material.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and dilute HCl (pH˜1)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography (EtOAc:heptane, 1:1)

Sources & evidence

ORD record
ord-42393328e08341c390fb201e86eb16b6
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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