Hydrochloric Acid → HCID 178476616, compound

HRID 419831Notes

Reaction equation

HRID 419831 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@H:6]1[O:7][C:8]1[C:9]([C:14]#[N:15])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:3])[CH3:2].[N:28]([Sn](C)(C)C)=[N+:29]=[N-:30].O.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:4][C@@H:5]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@H:6]1[O:7][C:8]1[C:9]([C:14]2[NH:30][N:29]=[N:28][N:15]=2)=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5104973Azido(trimethyl)stannaneHCID 12136250HCID 12136250, compound

Product 1

HCID 178476616HCID 178476616, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.682 g (1.73 mM) of 2-cyano-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation XV, and 1.24 g (6.05 mM) of azidotrimethyltin in 10 ml of toluene is prepared and this mixture is stirred at 70° C. for 7 days. After cooling, the reaction medium is poured onto a mixture of water and ethyl acetate and brought to pH 1 by addition of an N hydrochloric acid solution. The aqueous phase is extracted, brought to pH 5 by addition of a dilute sodium hydroxide solution and extracted with ethyl acetate. This organic phase is separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel, elution being carried out with a dichloromethane/methanol mixture (95/5;v/v). The expected compound is thus obtained in the form of a white foam (yield=30%).

Workup

  1. customobtained
  2. customis prepared
  3. temperatureAfter cooling
  4. extractionThe aqueous phase is extracted
  5. additionbrought to pH 5 by addition of a dilute sodium hydroxide solution
  6. extractionextracted with ethyl acetate
  7. customThis organic phase is separated
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product obtained
  12. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-6df15360237a4674a84d894d10e192bc
Source dataset
uspto-grants-2012_01
Patent number
US08093394B2

Reaction notes

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