Monobasic potassium phosphate → (S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carboxylic acid

HRID 216820Notes

Reaction equation

HRID 216820 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[C:8]([C@@H:14]([N:16]1[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]1=[O:26])[CH3:15])=[CH:7]2.[OH:27]P([O-])(O)=O.[K+].Cl([O-])=O.[Na+]>CC(=CC)C.CC(O)(C)C.C(Cl)Cl.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:27])=[O:13])[C:8]([C@@H:14]([N:16]1[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]1=[O:26])[CH3:15])=[CH:7]2

Participants

10

Reactant 3

HCID 516951Monobasic potassium phosphate2×HCID 23668197Sodium Chlorite2×HCID 57707962HCID 57707962, compound

Product 1

HCID 57707755(S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carboxylic acid

Reagents, catalysts & solvents 6

HCID 311Citric AcidSolventHCID 962WaterSolvent3×HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

To a stirred solution of (S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carbaldehyde (110 mg, 0.30 mmol) and potassium phosphate monobasic (41.0 mg, 0.30 mmol) in 2-methyl-2-butene (2 mL), tBuOH (2 mL), DCM (1.0 mL) and water (2.0 mL) was added sodium chlorite (27.3 mg, 0.30 mmol) in water (2.0 mL). The reaction was stirred at room temperature. for 2 hours and then it was treated with additional potassium phosphate monobasic (41.0 mg, 0.30 mmol) and sodium chlorite (27.3 mg, 0.30 mmol) in water (2.0 mL). The reaction was stirred for 2 hours and then it was diluted with 1.0 M citric acid (40 mL) and ethyl acetate (60 mL). The separated aqueous layer was extracted with ethyl acetate (2×60 mL) and the combined organic layers were washed with brine (40 mL), dried (MgSO4), filtered and evaporated in vacuo to give (S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)quinoline-2-carboxylic acid. 1H NMR (400 MHz, CDCl3) δ ppm 8.62 (1H, s), 7.72-7.84 (6H, m), 7.65 (1H, dd, J=5.3, 2.9 Hz), 6.80 (1H, q, J=7.0 Hz), 1.96 (3H, d, J=7.0 Hz). Mass Spectrum (ESI) m/e=381.0 (M+1).

Workup

  1. stirringThe reaction was stirred for 2 hours
  2. extractionThe separated aqueous layer was extracted with ethyl acetate (2×60 mL)
  3. washthe combined organic layers were washed with brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-70db7cbe8fc3407592730073cb2c0ef9
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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