Sodium Hydroxide → HCID 9955206, compound

HRID 1841291Notes

Reaction equation

HRID 1841291 reaction equation
[OH-].[Na+].[CH:3]1[C:14]2[C:13](=[CH:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=3)[C:12]3[CH:34]=[CH:35][CH:36]=[CH:37][C:11]=3[O:10][CH2:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)C>[CH:3]1[C:14]2[C:13](=[CH:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=3)[C:12]3[CH:34]=[CH:35][CH:36]=[CH:37][C:11]=3[O:10][CH2:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9804934HCID 9804934, compound

Product 1

HCID 9955206HCID 9955206, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 15% aqueous solution of NaOH (4 ml) was added to a solution of ethyl 3-(4-(2-(12H-dibenzo(d,g)-1,3-dioxocine-12-ylidene)ethoxy)phenyl)-2-ethoxypropionate (0.95 g, 2.0 mmol) in ethanol (15 ml), and the-mixture stirred at room temperature for 2 h, then left to stand overnight. The resulting solution was evaporated, water (20 ml) and benzene (25 ml) were added, and the mixture acidified to pH 6 with acetic acid. The benzene layer was separated, and the water layer further extracted with benzene (2×10 ml). The combined benzene extracts were washed with water (20 ml), brine (15 ml), dried (MgSO4) and evaporated to give 3-(4-(2-(12H-dibenzo(d,g)-1,3-dioxocine-12-ylidene)ethoxy)phenyl)-2-ethoxypropionic acid,: 0.79 g (83.2%). This acid (0.76 g, 1.6 mmol) was dissolved in acetone (30 ml), L-lysine (0.234 g, 1.6 mmol) and water (3 ml) were added and the mixture stirred at room temperature for 2 h. The solution was filtered, evaporated, and the residue stirred with a mixture of Et2O (20 ml) and acetone (20 ml) overnight. The resulting solid was collected by filtration, washed with Et2O (2×30 ml) and dried to give the title compound as a partial hydrate: 0.90 g (93.5%).

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe resulting solution was evaporated
  4. additionwater (20 ml) and benzene (25 ml) were added
  5. customThe benzene layer was separated
  6. extractionthe water layer further extracted with benzene (2×10 ml)
  7. washThe combined benzene extracts were washed with water (20 ml), brine (15 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-0b07a02719f8416eb64b479cdbb7a8c2
Source dataset
uspto-grants-2004_01
Patent number
US06683111B2

Reaction notes

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