Methyl iodide → (Rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

HRID 655507Notes

Reaction equation

HRID 655507 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([CH:19]([CH2:30][OH:31])[CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32]I.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([CH:19]([CH2:30][O:31][CH3:32])[CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:28])([CH3:27])[CH3:29])([CH3:25])[CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67080734(Rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

Product 1

HCID 67080682(Rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.37 g (3.04 mmol) of the above prepared (rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester and 0.95 ml (15.20 mmol) of methyl iodide were dissolved in 4.8 ml of N,N-dimethylformamide. After cooling (0° C.), 0.16 g (3.65 mmol) of NaH (55% in oil) was added. The reaction was stirred for 3 h at this temperature, then poured onto crushed ice/10% aq. potassium hydrogensulfate solution and extracted with diethyl ether (3×). The organic layers were washed with 10% aq. potassium hydrogensulfate solution and 10% aq. sodium chloride solution, dried over Na2SO4 and evaporated to dryness to yield 1.36 g (96%) of the title compound as light yellow oil. MS: 465.3 (MH+).

Workup

  1. additionwas added
  2. additionpoured
  3. extractionextracted with diethyl ether (3×)
  4. washThe organic layers were washed with 10% aq. potassium hydrogensulfate solution and 10% aq. sodium chloride solution
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-bfb7a7940a734eef801c8af5f8a11d5f
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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