Lithium Hydroxide → SL-84.0853

HRID 1185995Notes

Reaction equation

HRID 1185995 reaction equation
[OH-].[Li+].[CH3:3][N:4]([CH3:28])[C:5]([CH2:7][C:8]1[N:12]2[CH:13]=[C:14]([C:17]([O:19]C)=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:9]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)=[O:6]>O1CCCC1.C(Cl)(Cl)Cl.CO>[CH3:28][N:4]([CH3:3])[C:5]([CH2:7][C:8]1[N:12]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:9]=1[C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)=[O:6]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 16088234Cycloechinulin

Product 1

HCID 13691338SL-84.0853

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584188Chloroform methanolSolvent

Procedure

1M lithium hydroxide (84 ml, 15.4 mmol) was added dropwise to a solution of 6 (3.0 g, 8.53 mmol) in tetrahydrofuran (THF) (100 ml) and the solution stirred at room temperature overnight. Solvent was removed and the aqueous phase washed with chloroform, neutralized to pH 7 with 1M HCl and evaporated to dryness. The solid obtained was suspended in chloroform:methanol (9:1) (100 ml) and stirred for 1 h. The solid was removed by filtration, dried and purified by chromatography (chloroform:methanol, 9:1) to give hapten-I (1.67 g, 58%). NMR 13C(CD3OD) (d, ppm): 172.48, 171.05, 146.92, 146.09, 139.64, 132.69, 130.77, 130.01, 128.91, 127.9, 125.43, 117.55, 115.7, 38.27, 36.64, 30.53 and 21.71. MS: Mass formula (338.1503); Calc. Mass (338.1505).

Workup

  1. customSolvent was removed
  2. washthe aqueous phase washed with chloroform
  3. customevaporated to dryness
  4. customThe solid obtained
  5. stirringstirred for 1 h
  6. customThe solid was removed by filtration
  7. customdried
  8. custompurified by chromatography (chloroform:methanol, 9:1)
  9. customto give hapten-I (1.67 g, 58%)

Sources & evidence

ORD record
ord-7994a8c7eb81458fb414217e26b69fc2
Source dataset
uspto-grants-2014_03
Patent number
US08673652B2

Reaction notes

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