Methanol → 2,3-Dihydroxybutanedioic Acid

HRID 1861563Notes

Reaction equation

HRID 1861563 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:25][CH:26]([O:32][CH2:33][CH3:34])[C:27]([O:29]CC)=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:18][C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2.[CH3:35][OH:36].[OH-:37].[Na+].[OH2:39]>>[CH:26]([OH:32])([C:27]([OH:29])=[O:28])[CH:25]([OH:39])[C:35]([OH:37])=[O:36].[I:1][C:2]1[CH:3]=[C:4]([CH2:25][CH:26]([O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:18][C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 18624479HCID 18624479, compound3×

Product 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 18624481HCID 18624481, compound

Procedure

To a mixture of racemic ethyl 3-[3-iodo-4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropionate of the formula (4) (45 g) obtained according to the procedure described in step (vii) above and methanol (225 ml), was added aqueous 10% sodium hydroxide solution (225 ml) slowly at room temperature over a period of 10-15 minutes. The reaction mixture was stirred at the same temperature for a period of 2-4 h. The progress of the reaction was monitored by TLC. After the complete hydrolysis of the compound of the formula (4), the reaction mass was diluted with water (225 ml) and washed with toluene to remove the impurities. The aqueous layer was acidified with dilute hydrochloric acid and extracted with toluene. Combined toluene extracts were washed with water and concentrated under reduced pressure to half the volume and treated with activated charcoal. Filtration of the charcoal followed by concentration of toluene to ˜50 ml and precipitation with pet. ether afforded racemic acid of the formula (5) as an off-white to white solid, which was filtered and dried at room temperature (˜30° C.), (38-39 g, 90-92%).

Workup

  1. customobtained
  2. washwashed with toluene
  3. customto remove the impurities
  4. extractionextracted with toluene
  5. washCombined toluene extracts were washed with water
  6. concentrationconcentrated under reduced pressure to half the volume
  7. additiontreated with activated charcoal
  8. filtrationFiltration of the charcoal
  9. customfollowed by concentration of toluene to ˜50 ml and precipitation with pet. ether

Sources & evidence

ORD record
ord-f03c4fa73dd9430093d3644741d7b3f9
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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