Sodium Hydroxide → HCID 22864589, compound

HRID 1078514Notes

Reaction equation

HRID 1078514 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[CH:29]=[C:28]([C:33]([O:35]CC4C=CC=CC=4)=[O:34])[CH:27]=[CH:26]5)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][C@H:19]([OH:22])[CH2:20][OH:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+]>CO>[C:1]12([C:11]3[CH:12]=[C:13]([C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[CH:29]=[C:28]([C:33]([OH:35])=[O:34])[CH:27]=[CH:26]5)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][C@H:19]([OH:22])[CH2:20][OH:21])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22864590HCID 22864590, compound

Product 1

HCID 22864589HCID 22864589, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.45 g (6 mmol) of the benzyl ester obtained in Example 51, in 50 ml of methanol, are treated with 4 g of sodium hydroxide. The reaction medium is refluxed for 2 h and it is then treated as indicated in Example 6. After a recrystallization from the ethanol/water mixture, 2.28 g (87%) of the expected derivative are isolated, which derivative melts at 271°-272° C., [α]D =+1.5° (c=1,DMF).

Workup

  1. temperatureThe reaction medium is refluxed for 2 h
  2. additionit is then treated
  3. customAfter a recrystallization from the ethanol/water mixture, 2.28 g (87%) of the expected
  4. customderivative are isolated
  5. customwhich derivative melts at 271°-272° C., [α]D =+1.5° (c=1,DMF)

Sources & evidence

ORD record
ord-acebf0580f4c48ae936a18820ae4a922
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

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