Sodium Hydroxide → HCID 69414920, compound

HRID 852882Notes

Reaction equation

HRID 852882 reaction equation
OOS([O-])=O.[K+].[NH2:7][C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:11]=[CH:12][CH:13]=1.[OH-:23].[Na+].C([O-])(O)=[O:26].[Na+]>O.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.CC(C)=O>[N+:7]([C:8]1[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:11]=[CH:12][CH:13]=1)([O-:26])=[O:23]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfite2×HCID 69416241HCID 69416241, compound

Product 1

HCID 69414920HCID 69414920, compoundYield 31.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×HCID 6049Ethylenediaminetetraacetic AcidSolvent

Procedure

Acetone (14 mL) in water (17 mL) was added with simultaneous addition of a separate solution of Oxone (5.96 g, 9.7 mmol) dissolved in EDTA solution (0.0004 M, 35 mL) to a solution of 72 (500 mg, 1.9 mmol), NaOH (170 mg, 4.2 mmol) and NaHCO3 (1.63 g, 19 mmol) in water (30 mL) at 0-2° C. The Oxone solution was added at twice the rate of the acetone solution, and care was taken to ensure that the internal temperature was kept below 8°. After stirring overnight, Na2S2O5 solution was added (10% w/v, 50 mL) and the mixture extracted with EtOAc. The extract was washed with brine, dried over MgSO4 and the solvent removed in vacuo. Chromatography of the crude material (silica gel, 2:3 EtOAc:petroleum) afforded 73 (149 mg, 31%): 1H NMR (CDCl3) δ 1.36 (mn, 4H), 1.63 (m, 4H), 2.33 (t, J=7 Hz, 2H), 2.69 (t, J=8 Hz, 2H), 7.44 (m, 2H), 8.02 (m, 2H). 13C NMR (CDCl3) δ 180.2, 148.5, 144.7, 134.9, 129.3, 123.3, 121.1, 35.6, 34.1, 31.0, 28.93, 28.88, 24.7.

Workup

  1. customwas kept below 8°
  2. extractionthe mixture extracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f0d255d4880f4bc1bf97c054039795ea
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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