2,3-Dihydroxybutanedioic Acid → HCID 54055691, compound

HRID 726335Notes

Reaction equation

HRID 726335 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([Si](C(C)C)(C(C)C)C(C)C)[C:17]1[CH2:16][CH2:15][CH:14]([N:32]([CH3:34])[CH3:33])[CH2:13][C:12]2=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B(O)(O)O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C(C(C(O)=O)O)O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([N:32]([CH3:34])[CH3:33])[CH2:13][C:12]2=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 7628Boric AcidHCID 2724141Tetrabutylammonium FluorideHCID 54325774HCID 54325774, compound

Product 1

HCID 54055691HCID 54055691, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.44 gm (0.91 mMol) 6-(t-butoxycarbonyl)amino-3-(dimethyl)amino-9-triisopropylsilyl-1,2,3,4-tetrahydro-9H-carbazole in 10 mL tetrahydrofuran at 0° C. were added 0.30 gm boric acid followed by 1.5 mL 1M aqueous tetrabutylammonium fluoride. After 3 hours the reaction mixture was added to dilute aqueous tartaric acid and the resulting mixture extracted several times with dichloromethane. The remaining aqueous phase was made basic with dilute aqueous sodium hydroxide and extracted well with dichloromethane. This organic phase was dried over sodium sulfate and concentrated under reduced pressure. This residue was subjected to radial chromatography (2 mm silica gel), eluting with 96:4 chloroform:methanol containing 5% ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure to give 0.246 gm (83%) of the desired product.

Workup

  1. extractionthe resulting mixture extracted several times with dichloromethane
  2. extractionextracted well with dichloromethane
  3. dry with materialThis organic phase was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluting with 96:4 chloroform
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aed6c9b6d8244fa2b000263217d1f39e
Source dataset
uspto-grants-1998_01
Patent number
US05708187

Reaction notes

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