Water → HCID 15157489, compound

HRID 2371633Notes

Reaction equation

HRID 2371633 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[C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:36][CH2:37][C:38](=[O:44])[N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)([CH2:30][CH2:31][C:32]([O:34]C)=[O:33])[CH2:3]1.[OH-].[Na+].O>CO>[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[C:29]4[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:36][CH2:37][C:38](=[O:44])[N:39]2[CH2:40][CH2:41][CH2:42][CH2:43]2)([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15157488HCID 15157488, compound

Product 1

HCID 15157489HCID 15157489, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 240 mg (0.40 mmol) of the title product of Example 51 in 4 ml of methanol was added 0.15 ml of a 50% aqueous solution of sodium hydroxide and 1 ml of water. The mixture was stirred for 1 hour at reflux and then permitted to cool. The cooled reaction mixture was partitioned between ethyl acetate and 3N hydrochloric acid, and the aqueous layer was further extracted with two portions of ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. Chromatography of the residue over silica gel, using methanol/ethyl acetate/acetic acid as eluent, gave a glass which was triturated with diethyl ether to give the title compound (61 mg) as a solid, m.p. 160°-164° C.

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. customThe cooled reaction mixture
  4. customwas partitioned between ethyl acetate and 3N hydrochloric acid
  5. extractionthe aqueous layer was further extracted with two portions of ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customgave a glass which
  11. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-b88b803636fd4f548c0e58fa57d80e29
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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