Sodium Hydroxide → HCID 178440896, compound

HRID 977831Notes

Reaction equation

HRID 977831 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-7d814aa7c0be4807985234c4be9b12b5
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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