Acetone → HCID 86737820, compound

HRID 1680810Notes

Reaction equation

HRID 1680810 reaction equation
[CH3:1][O:2][C@H:3]1[C@H:9]([CH3:10])[O:8][C@@H:6]([OH:7])[CH2:5][C@H:4]1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14].[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].O.CC(C)=O>N1C=CC=CC=1>[CH3:1][O:2][C@H:3]1[C@H:9]([CH3:10])[O:8][CH:6]([O:7][C:25](=[O:26])[C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:29][CH:28]=2)[CH2:5][C@H:4]1[NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 85024-Nitrobenzoyl chlorideHCID 86737819HCID 86737819, compound

Product 1

HCID 86737820HCID 86737820, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.64 g; 6.38 mmol of compound VII in 76 ml of anhydrous pyridine was treated at 0° C. under stirring with 2 g of p-nitrobenzoyl chloride. After 30 minutes at 0° C. and then 20 hours at room temperature, the reaction mixture was poured into iced water and extracted with chloroform; the combined chloroform extracts were washed successively with a 10% potassium bisulphate solution, 10% sodium bicarbonate solution and finally with water, after which it was dried over anhydrous sodium sulphate and then concentrated to a residue. The residue was chromatographed on a silica gel column. Elution with a chloroform: acetone mixture (95:5 by volume) gave 1.76 g (yield 68%) of 4-O-methyl-1-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-L-ribohexopyranose (VIII).

Workup

  1. extractionextracted with chloroform
  2. washthe combined chloroform extracts were washed successively with a 10% potassium bisulphate solution, 10% sodium bicarbonate solution and finally with water
  3. dry with materialafter which it was dried over anhydrous sodium sulphate
  4. concentrationconcentrated to a residue
  5. customThe residue was chromatographed on a silica gel column
  6. washElution with a chloroform

Sources & evidence

ORD record
ord-1e15b87f748042b99becfc2c52118025
Source dataset
uspto-grants-1981_06
Patent number
US04276289

Reaction notes

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