Pyridine → HCID 86751790, compound

HRID 1941452Notes

Reaction equation

HRID 1941452 reaction equation
[NH:1]([CH2:5][C@@H:6]1[O:18][C@H:17]([CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)[C:2]([NH2:4])=[O:3].N1C=CC=CC=1.[CH3:34][C:35](=[CH:39][O:40][CH3:41])[C:36](Cl)=[O:37].P(O)(O)([O-])=O.[K+]>C(Cl)Cl>[CH3:34][C:35](=[CH:39][O:40][CH3:41])[C:36]([N:1]([CH2:5][C@@H:6]1[O:18][C@H:17]([CH2:19][O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@@H:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)[C:2]([NH2:4])=[O:3])=[O:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 516951Monobasic potassium phosphateHCID 53969872HCID 53969872, compoundHCID 67726207HCID 67726207, compound

Product 1

HCID 86751790HCID 86751790, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 32.2 ml of methylene chloride was dissolved 2.3 g of 1-ureido-2,5-anhydro-4,6-di-O-benzyl-1,3-dideoxy-D-allitol followed by addit ion of 9.2 ml of pyridine. Then, 1.67 g of 2-methyl-3-methoxypropenoyl chloride was added and the mixture was stirred at room temperature overnight. This reaction mixture was poured in 5% aqueous solution of monopotassium phosphate followed by extraction with ethyl acetate. The organic layer was washed with 5% aqueous monopotassium phosphate solut ion thrice, saturated aqueous sodium hydrogen carbonate solution once, and saturated aqueous sodium chloride solution once in turn, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (chloroform→1% methanol/chloroform) to provide 2.3 g of the desirable compound as pale-yellow oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with 5% aqueous monopotassium phosphate solut ion thrice, saturated aqueous sodium hydrogen carbonate solution once
  3. dry with materialsaturated aqueous sodium chloride solution once in turn, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography (chloroform→1% methanol/chloroform)

Sources & evidence

ORD record
ord-08b547d15b2249809d498b2e2423f18e
Source dataset
uspto-grants-1997_12
Patent number
US05703224

Reaction notes

Loading…