Sodium Hydroxide → HCID 77324662, compound

HRID 233815Notes

Reaction equation

HRID 233815 reaction equation
C([O:3][C:4]([C:6]1([C:31]([O:33]CC)=[O:32])[O:10][C:9]2[C:11]3[CH2:12][CH:13]([N:18]4[CH2:22][CH:21]([C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=5)[O:20]C4=O)[CH2:14][C:15]=3[CH:16]=[CH:17][C:8]=2[O:7]1)=[O:5])C.[OH-].[Na+:37]>>[Na+:37].[Na+:37].[Cl:29][C:25]1[CH:24]=[C:23]([CH:21]([OH:20])[CH2:22][NH:18][CH:13]2[CH2:12][C:11]3[C:9]4[O:10][C:6]([C:4]([O-:5])=[O:3])([C:31]([O-:33])=[O:32])[O:7][C:8]=4[CH:17]=[CH:16][C:15]=3[CH2:14]2)[CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54449292HCID 54449292, compound

Product 1

HCID 77324662HCID 77324662, compound

Procedure

To 1.60 g of product from Example 1, Step C, under argon, is added 22 ml of 2.5N sodium hydroxide. The reaction mixture is heated to its reflux temperature and maintained at this temperature for 20 hours. The gum that is originally present dissolves and the solution turns a dark brown. The reaction mixture is evaporated in vacuo and the residue treated with ethyl alcohol. The solids are isolated by filtration, rinsed with ethyl alcohol and diethyl ether and air dried briefly. The resulting solid is dissolved in water and loaded onto a column of XAD-4 resin (previously washed with 1 liter of 50:50 methyl alcohol:water, followed by 500 ml of water). The column is eluted with 1 liter of water followed by 1 liter of methyl alcohol. The methyl alcohol fractions containing the Rf 0.60 component (7:1 water:methyl alcohol; reverse phase tlc plates) are combined, evaporated in vacuo and the residue is triturated with ethyl alcohol. The solids are collected, rinsed with ethyl alcohol and air dried to give 0.86 g of the desired product as a light brown solid. 1H NMR(D2O): δ2.79(m,2H); 3.01(m,2H); 3.21(m,2H); 3.79(m,1H); methine next to OH approx. 4.86; 6.77(s,2H,Ar); 7.3-7.5(m,4H,Ar).

Workup

  1. temperatureThe reaction mixture is heated to its
  2. temperaturereflux temperature
  3. temperaturemaintained at this temperature for 20 hours
  4. dissolutionThe gum that is originally present dissolves
  5. customThe reaction mixture is evaporated in vacuo
  6. additionthe residue treated with ethyl alcohol
  7. customThe solids are isolated by filtration
  8. washrinsed with ethyl alcohol and diethyl ether and air
  9. customdried briefly
  10. dissolutionThe resulting solid is dissolved in water
  11. washpreviously washed with 1 liter of 50:50 methyl alcohol
  12. washThe column is eluted with 1 liter of water
  13. additionThe methyl alcohol fractions containing the Rf 0.60 component (7:1 water:methyl alcohol; reverse phase tlc plates)
  14. customevaporated in vacuo
  15. customthe residue is triturated with ethyl alcohol
  16. customThe solids are collected
  17. washrinsed with ethyl alcohol and air
  18. customdried

Sources & evidence

ORD record
ord-9a1922ba9946420b802a25d87a91421c
Source dataset
uspto-grants-1997_01
Patent number
US05594027

Reaction notes

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