Methyl iodide → HCID 57947604, compound

HRID 340905Notes

Reaction equation

HRID 340905 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].IC.[H-].[Na+].[CH3:30]COC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]([CH3:30])[C@H:9]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 57947507HCID 57947507, compound

Product 1

HCID 57947604HCID 57947604, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (S)-methyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsilyloxy)hexanoate (15 g, 40 mmol) in DMF (100 mL) was added iodomethane (17 g, 120 mmol, 3 equiv.) at 0° C. NaH (60%, 2.4 g, 60 mmol, 1.5 equiv.) was added in 3 portions. The reaction was stirred at RT for 2 h. EtOAc (150 mL) and brine (200 mL) were added to the reaction mixture. The organic layer was washed with brine (200 mL), dried, and concentrated to give (S)-methyl 5-(tert-butoxycarbonyl(methyl)amino)-6-(tert-butyldimethylsilyloxy)hexanoate (15.5 g, quant.) as a colorless oil. LRMS (M-Boc+H+) m/z 290.1.

Workup

  1. washThe organic layer was washed with brine (200 mL)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a8aded328097458dbad03c074f8764bb
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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