Dimethyl Sulfoxide → HCID 86754800, compound

HRID 1602847Notes

Reaction equation

HRID 1602847 reaction equation
CS(C)=[O:3].Cl.C[N:7](C)[CH2:8][CH2:9][CH2:10]N=C=N[CH2:14][CH3:15].F[C:18](F)(F)[C:19]([O-:21])=[O:20].[NH+]1C=CC=CC=1.[OH-:30].[Na+]>C(Cl)Cl.O.C(OCC)(=O)C>[C:19]([O:21][CH2:14][CH3:15])(=[O:20])[CH3:18].[CH3:8][C:9]([CH3:10])=[O:3].[OH-:30].[NH4+:7]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9813011pyridine TFA

Product 1

HCID 86754800HCID 86754800, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5.9 g (7.4 mmol) of 2'-O-Acetyl-9-deoxo-8a-aza-8a-methyl-8a-homoerythromycin A in 100 ml of dry methylene chloride under nitrogen at room temperature was successively added 5.3 ml (74.7 mmol) of dimethyl sulfoxide, 7.15 g (19.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 7.15 g (37 mmol) of pyridinium trifluoroacetate. The reaction mixture was stirred for 2 hours, at which point 300 ml of ethyl acetate followed by 100 ml of water was added. The pH of the solution was adjusted to the range of 9-10 with 1N sodium hydroxide solution. The ethyl acetate layer was washed with brine, dried (anhydrous sodium sulfate) and evaporated. Silica chromatography with ethyl acetate-acetone-ammonium hydroxide (9:1:0.1) gave 4.8 g (82% yield) of the title compound as a white solid.

Workup

  1. customat room temperature
  2. additionwas added
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-449ece1c53544c1ca83a7021c417a81a
Source dataset
uspto-grants-1999_11
Patent number
US05985844

Reaction notes

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