2,3-Dihydroxybutanedioic Acid → HCID 53698866, compound

HRID 1734916Notes

Reaction equation

HRID 1734916 reaction equation
B(F)(F)F.CCOCC.[CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[CH:20][C:21](OCC)=[O:22])[C:14]=1[NH:26][C:27](=[O:43])[CH2:28][CH:29]1[C:42]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[O:36][C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)([CH3:12])[CH3:11].[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)C(C(C(O)=O)O)O>C(Cl)Cl>[CH:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[CH:20][CH2:21][OH:22])[C:14]=1[NH:26][C:27](=[O:43])[CH2:28][CH:29]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=2[O:36][C:37]2[C:42]1=[CH:41][CH:40]=[CH:39][CH:38]=2)([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 8000Boron trifluoride etherateHCID 21225700DiisobutylaluminumhydrideHCID 53716971HCID 53716971, compound

Product 1

HCID 53698866HCID 53698866, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

68 μl (0.60 mmol) of boron trifluoride etherate were added at -78° C. to a solution of 228 mg (0.5 mmol) of N-[2-isopropyl-6-(2-ethoxycarbonylethenyl)phenyl]-2-(9H-xanthen-9-yl)acetamide [prepared as described in step (i) above] in 6 ml of methylene chloride. The resulting mixture was stirred for 30 minutes, after which 2.0 ml of a 1.0M solution of diisobutylaluminum hydride were added dropwise over a period of 5 minutes. The temperature of the mixture was allowed to rise to room temperature, and then 10 ml of a 10% w/v aqueous solution of tartaric acid were added to the reaction mixture in order to stop the reaction. The reaction mixture was then diluted with methylene chloride. The diluted mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and then with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was triturated with a mixture of diethyl ether and hexane to cause crystallization. The crystals were collected by filtration to give 185 mg (yield 85%) of the title alcohol derivative, melting at 225°-227° C. (after recrystallization from a mixture of acetonitrile and diisopropyl ether).

Workup

  1. customto rise to room temperature
  2. customthe reaction
  3. washThe diluted mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe resulting residue was triturated with a mixture of diethyl ether and hexane
  7. customcrystallization
  8. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-3065e7817b7c42c48473bc8c469f30a7
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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