Water → HCID 86713388, compound

HRID 921269Notes

Reaction equation

HRID 921269 reaction equation
Br[CH2:2][C:3]1[C:4]([N+:15]([O-:17])=[O:16])=[C:5]([CH:12]=[CH:13][CH:14]=1)[C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7].C(=O)([O-])[O-:19].[Ca+2].O>O1CCOCC1>[OH:19][CH2:2][C:3]1[C:4]([N+:15]([O-:17])=[O:16])=[C:5]([CH:12]=[CH:13][CH:14]=1)[C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 10112Calcium CarbonateHCID 86713387HCID 86713387, compound

Product 1

HCID 86713388HCID 86713388, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Intermediate 37B (3.7 g, 4.88 mmol) and calcium carbonate (2.93 g, 29.3 mmol) in dioxane (25 mL)/water (25 mL) was stirred at reflux for 5 h. The mixture was then cooled to room temperature, the solid was removed by filtration and the filtrate was extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to dryness. The crude residue was purified by flash chromatography (SiO2, 80 g column, EtOAc/hexane=20-100%) to afford Intermediate 37C (1.079 g, 78%). HPLC: RT=0.75 min (CHROMOLITH® SpeedROD column 4 6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm), MS(ES): m/z=241.0 [M+H+].

Workup

  1. temperatureat reflux for 5 h
  2. customthe solid was removed by filtration
  3. extractionthe filtrate was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude residue was purified by flash chromatography (SiO2, 80 g column, EtOAc/hexane=20-100%)

Sources & evidence

ORD record
ord-2f454d725c6c408b9240c963afe207bb
Source dataset
uspto-grants-2016_03
Patent number
US09273014B2

Reaction notes

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