Hydrochloric Acid → HCID 19822202, compound

HRID 1030380Notes

Reaction equation

HRID 1030380 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:36]=[CH:35][C:12]([O:13][CH2:14][C:15]3([CH3:34])[CH2:24][C:23](=[O:25])[C:22]4[C:17](=[C:18]([CH3:33])[C:19]([CH3:32])=[C:20]([O:27][CH2:28][C:29]([OH:31])=[O:30])[C:21]=4[CH3:26])[O:16]3)=[CH:11][CH:10]=2)[S:3]1.O1CCO[CH2:39][CH2:38]1.Cl.C(=O)(O)[O-].[Na+]>O.C(O)C>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]3([CH3:34])[CH2:24][C:23](=[O:25])[C:22]4[C:17](=[C:18]([CH3:33])[C:19]([CH3:32])=[C:20]([O:27][CH2:28][C:29]([O:31][CH2:38][CH3:39])=[O:30])[C:21]=4[CH3:26])[O:16]3)=[CH:35][CH:36]=2)[S:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 19822244HCID 19822244, compound

Product 1

HCID 19822202HCID 19822202, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.5 g of α-{2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-2,5,7,8-tetramethyl-4-oxo-chroman-6-yloxy}acetic acid (obtained as described in Example 59), 0.5 ml of a 4N dioxane solution of hydrogen chloride and 5 ml of ethanol was allowed to stand overnight at room temperature. The reaction mixture was then poured into water and the solution was neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was subjected to preparative silica gel thin layer chromatography (developing solvent, benzene:ethyl acetate=7:3 by volume) to obtain the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a67a865c8c2e47e8a5864b99b4e8bf21
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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