2,3-Dihydroxybutanedioic Acid → HCID 86744818, compound

HRID 1493291Notes

Reaction equation

HRID 1493291 reaction equation
[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH2:21][OH:22])[CH:16]=[CH:17][CH:18]=3)=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:39]O)(C)(C)C.C(O)(=O)C(C(C(O)=O)O)O>ClCCl.C1(C)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:29]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:8]2[N:12]=[N:11][C:10]([C:13]3[CH:14]=[C:15]([C@@H:19]4[O:39][C@H:20]4[CH2:21][OH:22])[CH:16]=[CH:17][CH:18]=3)=[N:9]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

8

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 6410tert-Butyl hydroperoxideHCID 53917552HCID 53917552, compound

Product 1

HCID 86744818HCID 86744818, compound

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolventHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent3×

Procedure

L-(+)-Dimethyl tartrate (1.85 g) was added in dry dichloromethane (10 ml) dropwise to a stirred solution of titanium (IV) isopropoxide (3.1 ml) in dry dichloromethane (30 ml) at -20° to -25° C. under nitrogen. The solution was stirred for 10 minutes and a solution of 3-[3-(2-triphenylmethyl-2H-tetrazol-5-yl)phenyl]-2-propenol (4.5 g) in dry dichloromethane (20 ml) was added, followed by a 3.7M solution of t-butylhydroperoxide in toluene (6.7 ml), both at -20° to -25° C. The pale orange solution was left to stand in a freezer for 3 hours. To the stirred solution was added aqueous tartaric acid (10%; 50 ml) and the mixture stirred for 1 hour, filtered and separated. The dichloromethane layer was dried over magnesium sulphate filtered and evaporated under reduced pressure to give a yellow oil. The oil was dissolved in carbon tetrachloride, washed with water, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a pale yellow oil. The oil was chromatographed on a silica gel column using diethyl ether and hexane (2:1) and the required fractions evaporated under reduced pressure to give a colourless crystalline solid.

Workup

  1. customat -20° to -25° C
  2. waitThe pale orange solution was left
  3. waitto stand in a freezer for 3 hours
  4. stirringthe mixture stirred for 1 hour
  5. filtrationfiltered
  6. customseparated
  7. dry with materialThe dichloromethane layer was dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give a yellow oil
  11. washwashed with water
  12. dry with materialdried over magnesium sulphate
  13. filtrationfiltered
  14. customevaporated under reduced pressure
  15. customto give a pale yellow oil
  16. customThe oil was chromatographed on a silica gel column
  17. customthe required fractions evaporated under reduced pressure
  18. customto give a colourless crystalline solid

Sources & evidence

ORD record
ord-b466501be67746e9a484536721047520
Source dataset
uspto-grants-1991_06
Patent number
US05021441

Reaction notes

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