2,6-Lutidine → HCID 25006393, compound

HRID 1175671Notes

Reaction equation

HRID 1175671 reaction equation
C([O:3][P:4]([CH2:9][O:10][C@:11]1([CH3:26])[C@@H:15]([OH:16])[C@@H:14]([OH:17])[C@H:13]([N:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[N:20][C:19]2=[O:25])[O:12]1)(=[O:8])[O:5]CC)C.N1C(C)=CC=CC=1C.C[Si](I)(C)C>C(#N)C>[NH2:24][C:21]1[CH:22]=[CH:23][N:18]([C@@H:13]2[O:12][C@:11]([CH3:26])([O:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])[C@@H:15]([OH:16])[C@H:14]2[OH:17])[C:19](=[O:25])[N:20]=1

Participants

5

Reactant 3

HCID 79372,6-Lutidine2×HCID 85247Trimethylsilyl iodideHCID 25006396HCID 25006396, compound

Product 1

HCID 25006393HCID 25006393, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 30.5 (112 mg, 0.29 mmol) in acetonitrile (10 mL) was added 2,6-lutidine (0.20 mL, 1.7 mmol) and then trimethylsilyl iodide (0.41 mL, 2.8 mmol). The mixture was stirred at room temperature for 1 h. After the reaction was done, 0.30 mL of 2,6-lutidine was added to the mixture and the mixture was concentrated under reduced pressure. The residue was then put into solution with water (3 mL) and treated with sodium hydroxide 1N to pH=10. The solution was then acidify to pH=3 using acetic acid and subjected to a reverse phase (YMC-Pack ODS-A) to give compound 30.6 (69 mg, 72% yield). 1H NMR (300 MHz, D2O): δ 1.39 (s, 3H), 3.54 (m, 2H), 3.99 (d, 1H, J=4.6), 4.63 (m, 1H), 6.09 (d, 1H, J=7.0), 6.14 (d, 1H, J=7.0), 8.0 (d, 1H, J=7.6). LRMS (ESI) MH+ C10H16N3O8P requires 338.2. Found 337.8.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additiontreated with sodium hydroxide 1N to pH=10

Sources & evidence

ORD record
ord-83c2de64b98c42e29240e99fb257ff1d
Source dataset
uspto-grants-2010_11
Patent number
US07842672B2

Reaction notes

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