Ethyl Acetate → N-[2-(tert-butyldimethylsilyloxy)ethyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]glycine amide

HRID 2303358Notes

Reaction equation

HRID 2303358 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]([CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36]([C:40]2[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=2)[CH:35]=1)[C:12](=[O:32])[CH2:13][NH:14]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(OCC)(=O)C>C(#N)C.N1CCCCC1>[Si:1]([O:8][CH2:9][CH2:10][N:11]([CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[C:36]([C:40]2[CH:41]=[C:42]([O:50][CH3:51])[C:43]([O:48][CH3:49])=[C:44]([O:46][CH3:47])[CH:45]=2)[CH:35]=1)[C:12](=[O:32])[CH2:13][NH2:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86758398N-[2-(tert-butyldimethylsilyloxy)ethyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-Nalpha-(9-fluorenylmethoxycarbonyl)glycine amide

Product 1

HCID 86758399N-[2-(tert-butyldimethylsilyloxy)ethyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]glycine amide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8082PiperidineSolvent

Procedure

N-[2-(tert-butyldimethylsilyloxy)ethyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-Nα-(9-fluorenylmethoxycarbonyl)glycine amide (5.15 g) was dissolved in a 20% acetonitrile solution (40 mL) of piperidine, and the solution was stirred at room temperature for 4 hours. Ethyl acetate was added to the reaction mixture, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1) to obtain the title compound.

Workup

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-1ba66145134c485fa594ac991eb183c1
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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