Methyl iodide → 3-(Tert-butoxycarbonyl(methyl)amino)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoic acid

HRID 1944151Notes

Reaction equation

HRID 1944151 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:32]I.[H-].[Na+]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]([CH3:32])[CH2:9][CH:10]([C:14]1[CH:15]=[CH:16][C:17]([CH2:20][O:21][Si:22]([CH:23]([CH3:24])[CH3:25])([CH:26]([CH3:28])[CH3:27])[CH:29]([CH3:31])[CH3:30])=[CH:18][CH:19]=1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 595637683-((tert-Butoxycarbonyl)amino)-2-(4-(((triisopropylsilyl)oxy)methyl)phenyl)propanoic acid

Product 1

HCID 595637453-(Tert-butoxycarbonyl(methyl)amino)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-(tert-butoxycarbonylamino)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoic acid (E203) in THF under N2 and cooled to 0° C. was added CH3I followed by NaH and the solution was warmed and allowed to stir for 18 h. The mixture was taken up in EtOAc and extracted with NH4Cl (sat), dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-10% MeOH/CH2Cl2 gradient) gave pure 3-(tert-butoxycarbonyl(methyl)amino)-2-(4-((tnisopropylsilyloxy)methyl)phenyl)propanoic acid (E204).

Workup

  1. temperaturethe solution was warmed
  2. extractionextracted with NH4Cl (sat)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-13a00f1cdb14459d87464040dfaf9d4d
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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