Sodium Hydroxide → HCID 15157434, compound

HRID 2371616Notes

Reaction equation

HRID 2371616 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:32][CH2:33][C:34]([O:36]C)=[O:35])([CH2:26][CH2:27][C:28]([O:30]C)=[O:29])[CH2:3]1.[OH-].[Na+]>O>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15157433HCID 15157433, compound

Product 1

HCID 15157434HCID 15157434, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 611 mg (1.19 mmol) of the title product of Example 16, 0.72 ml of 50% aqueous sodium hydroxide, and 11.7 ml of water was stirred at reflux. After one hour, another 2 ml of water was added and the reaction mixture was heated for an additional 2 hours. The mixture was allowed to cool and then partitioned between 75 ml of ethyl acetate and 50 ml of 3N hydrochloric acid. The aqueous layer was further extracted twice with 25 ml aliquots of ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered, and solvent removed on a rotary evaporator to give 501 mg of title product, m.p. 161.5°-162° C.

Workup

  1. temperatureat reflux
  2. temperaturethe reaction mixture was heated for an additional 2 hours
  3. temperatureto cool
  4. custompartitioned between 75 ml of ethyl acetate and 50 ml of 3N hydrochloric acid
  5. extractionThe aqueous layer was further extracted twice with 25 ml aliquots of ethyl acetate
  6. washThe combined organic extracts were washed with water, with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customsolvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-5e67dee3fe6d4f4491f00e3f65353c03
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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