Water → HCID 118098706, compound

HRID 708850Notes

Reaction equation

HRID 708850 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[CH:23](C(OCC)=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].O>CS(C)=O.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:12])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 118101242HCID 118101242, compound

Product 1

HCID 118098706HCID 118098706, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

15A (2.668 g, 5.82 mmol) was dissolved in DMSO (30 mL), lithium chloride (0.493 g, 11.64 mmol) and water (0.105 mL, 5.82 mmol) were added. The reaction mixture was stirred at 130° C. for 3 h, cooled to rt, diluted with EtOAc (150 mL), washed with water (2×50 mL), brine (1×50 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-60% EtOAc/hexanes). Fractions were combined and concentrated under reduced pressure to give 15B (2.062 g, 92% yield) as a yellowish oil. MS (ESI) m/z: 387.2 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 8.11 (1H, d, J=8.34 Hz), 8.06 (1H, br. s.), 7.28-7.46 (6H, m), 5.20 (2H, br. s.), 4.55-4.69 (2H, m), 4.13 (2H, d, J=6.82 Hz), 3.64-3.86 (2H, m), 2.92 (3H, s), 1.24 (3H, td, J=7.07, 2.53 Hz).

Workup

  1. temperaturecooled to rt
  2. washwashed with water (2×50 mL), brine (1×50 mL)
  3. dry with materialdried (Na2SO4)
  4. customEtOAc was removed under reduced pressure
  5. customthe residue was purified by flash chromatography (0-60% EtOAc/hexanes)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a165050c8acc49a99ffdbc92a58dade7
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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