Hydrochloric Acid → HCID 44626297, compound

HRID 509176Notes

Reaction equation

HRID 509176 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:15]3[CH:16]=[CH:17][C:18]4[O:22][CH2:21][CH2:20][C:19]=4[CH:23]=3)[C:11](OC)=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[NH2:24][OH:25].[OH-].[K+].[OH-].[Na+].Cl>C(OCC)(=O)C.CO.C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:15]3[CH:16]=[CH:17][C:18]4[O:22][CH2:21][CH2:20][C:19]=4[CH:23]=3)[C:11]([NH:24][OH:25])=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 57779657HCID 57779657, compound

Product 1

HCID 44626297HCID 44626297, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2 (380 mg, 1.22 mmol) and hydroxylamine (50% in water, 1.25 mL) in a 1:1 THF:methanol (10 mL) was added base (KOH (275 mg, 4.9 mmol) or NaOH). The mixture was stirred at room temperature for 2 h, acidified to pH 7 with 1M HCl solution, diluted with ethyl acetate and washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was triturated with 50% ethyl acetate:hexanes, filtered, and rinsed with hexanes to afford compound 3 as a white solid (170 mg, 45%). 1H NMR (DMSO-d6) δ (ppm): 10.81 (br s, 1H), 8.88 (br s, 1H), 7.16 (d, J=1.0 Hz, 2H), 6.99 (dd, J=8.4, 1.8 Hz, 2H), 6.67 (d, J=8.1 Hz, 2H), 4.53-4.45 (m, 5H), 3.12 (t, J=8.6 Hz, 4H). LRMS (ESI): (calc) 311.1 (found) 310.3 (M)−.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with 50% ethyl acetate
  7. filtrationhexanes, filtered
  8. washrinsed with hexanes

Sources & evidence

ORD record
ord-b8d37d34750f4941928f9713b8e3fd7b
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

Loading…