Sodium Hydroxide → HCID 178440896, compound

HRID 1734873Notes

Reaction equation

HRID 1734873 reaction equation
[C:1]([O:8][CH:9]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[C:23]([NH:31][C:32](=[O:48])[CH2:33][CH:34]2[C:47]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[O:41][C:40]3[C:35]2=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:22]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+:50]>>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH:9]([Na:50])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:22][C:23]=1[NH:31][C:32](=[O:48])[CH2:33][CH:34]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=2[O:41][C:42]2[C:47]1=[CH:46][CH:45]=[CH:44][CH:43]=2)([CH3:28])([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 19966036HCID 19966036, compound

Product 1

HCID 178440896HCID 178440896, compound

Procedure

4 ml of a methanolic solution containing 165 mg (0.255 mmol) of 1-{4-t-butyl-3-[2-(9H-xanthen-9-yl)acetamido]phenyl}-6-phenylhexyl hydrogen succinate (prepared as described in Example 54) were cooled in an ice bath, and then 2.42 ml (0.242 mmol) of a 0.1N aqueous solution of sodium hydroxide was added dropwise. The reaction solution was condensed by evaporation under reduced pressure, whilst keeping its temperature below 15° C. 20 ml of toluene were added to the residue, and then sufficient ethanol was added until the solution became homogenous. The solvent was then was removed by distillation under reduced pressure. In order to remove any remaining water, toluene was added to the residue and the mixture was distilled again. This procedure was repeated several times, and gave 170 mg (a quantitative yield) of the title compound as a foam-like substance.

Workup

  1. temperaturewere cooled in an ice bath
  2. customcondensed
  3. customby evaporation under reduced pressure
  4. customits temperature below 15° C
  5. addition20 ml of toluene were added to the residue
  6. additionsufficient ethanol was added until the solution
  7. customThe solvent was then was removed by distillation under reduced pressure
  8. customIn order to remove any remaining water, toluene
  9. additionwas added to the residue
  10. distillationthe mixture was distilled again

Sources & evidence

ORD record
ord-b1d233ab3e234bc9b58a09222ffd6d99
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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