Pyridine → HCID 69804279, compound

HRID 488646Notes

Reaction equation

HRID 488646 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]([CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N+:21]([O-:23])=[O:22])=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8])=[O:4].N1C=CC=CC=1.[CH3:30][Si:31]([CH3:36])([CH3:35])[CH2:32][CH2:33]O.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH3:30][Si:31]([CH3:36])([CH3:35])[CH2:32][CH2:33][O:8][C:7](=[O:9])[CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N+:21]([O-:23])=[O:22])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 180132-(Trimethylsilyl)ethanolHCID 22271898HCID 22271898, compound

Product 1

HCID 69804279HCID 69804279, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-methoxycarbonylamino-3-(4-nitro-naphthalen-1-yl)-propionic acid (0.35 g, 1.1 mmol), pyridine (0.78 mL) and 2-trimethylsilylethanol (0.18 mL, 1.25 mmol, 1.1 eq) in acetonitrile (1.1 mL) cooled in an ice bath was added dicyclohexylcarbodiimide (0.25 g, 1.21 mmol). The mixture was stirred cold for 1 hour, placed in the refrigerator for 14 hours. The reaction mixture was filtered, concentrated under reduced pressure and purified on silica gel eluting with heptane/ethyl acetate (4:1) to provide the titled compound. MS ESI(−)) m/e 417 (M−H)−.

Workup

  1. temperaturecooled in an ice bath
  2. waitplaced in the refrigerator for 14 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. custompurified on silica gel eluting with heptane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-83c81e26247840328c7f2013da31a54b
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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