2,3-Dihydroxybutanedioic Acid → 2,3-Dihydroxybutanedioate

HRID 35348Notes

Reaction equation

HRID 35348 reaction equation
[NH2:1][C:2]([CH:4]1[N:9]([CH2:10][CH2:11][CH2:12][CH:13]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:8][CH2:7][N:6]([CH2:28][C:29]([NH:31][C:32]2[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:39])=[O:30])[CH2:5]1)=[O:3].[OH:40][CH:41]([CH:45]([OH:49])[C:46]([OH:48])=[O:47])[C:42]([OH:44])=[O:43]>C(O)C>[NH2:1][C:2]([CH:4]1[N:9]([CH2:10][CH2:11][CH2:12][CH:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[CH2:8][CH2:7][N:6]([CH2:28][C:29]([NH:31][C:32]2[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:39])=[O:30])[CH2:5]1)=[O:3].[OH:40][CH:41]([CH:45]([OH:49])[C:46]([O-:48])=[O:47])[C:42]([O-:44])=[O:43]

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 142300883-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)butyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide

Product 2

HCID 38061142,3-DihydroxybutanedioateHCID 142300883-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)butyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3 parts of 3-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)butyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide in 24 parts of ethanol was added a solution of 0.94 parts of (+)-2,3-dihydroxybutanedioic acid in 24 parts of ethanol. The whole was evaporated and the oily residue was dissolved in warm 4-methyl-2-pentanone. After cooling to 0° C., the product was filtered off and dissolved in 2-propanone. 0.2 Parts of 2,3-dihydroxybutanedioic acid were added and upon the addition of 4-methyl-2-pentanone, the product was precipitated. It was filtered off and dried, yielding 0.8 parts of (+)-3-(aminocarbonyl)-4-[4,4-bis(4-fluorophenyl)butyl]-N-(2,6-dimethylphenyl)-1-piperazineacetamide [R-(R*,R*)]-2,3-dihydroxybutanedioate (2:3) monohydrate; mp. 78.1° C. (compound 173).

Workup

  1. customThe whole was evaporated
  2. dissolutionthe oily residue was dissolved in warm 4-methyl-2-pentanone
  3. filtrationthe product was filtered off
  4. dissolutiondissolved in 2-propanone
  5. addition0.2 Parts of 2,3-dihydroxybutanedioic acid were added and upon the addition of 4-methyl-2-pentanone
  6. customthe product was precipitated
  7. filtrationIt was filtered off
  8. customdried

Sources & evidence

ORD record
ord-a74d9d077e6941f5a1586fa85bdf3173
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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