Methyl iodide → HCID 66783051, compound

HRID 1096222Notes

Reaction equation

HRID 1096222 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([N:14]1[C:20](=[O:21])[CH2:19][CH2:18][N:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:16][CH2:15]1)[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32]I.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([N:14]1[C:20](=[O:21])[CH2:19][CH2:18][N:17]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=2)[CH2:16][CH2:15]1)[CH2:12][O:13][CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66783193HCID 66783193, compound

Product 1

HCID 66783051HCID 66783051, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.40 g (0.92 mmol) of the above prepared 4-((S)-3-benzyloxy-1-hydroxymethyl-propyl)-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one and 0.29 ml (4.58 mmol) of methyl iodide were dissolved in 1.6 ml of DMF. After cooling (0° C.), 0.048 g (1.10 mmol) of NaH (55% dispersion in oil) was added. The reaction was stirred for 3 h at this temperature, then poured onto crashed ice/aq. 10% KHSO4 solution and extracted with Et2O (3×). The organic layers were washed with aq. 10% KHSO4 solution and aq. 10% NaCl solution, dried over Na2SO4, evaporated and purified by flash silica gel column (n-heptane:EtOAc 1:1) to yield 0.42 g (quantitative) of the title compound as light yellow oil. MS: 451.2 (MH+, 1Cl).

Workup

  1. additionwas added
  2. additionpoured
  3. extraction10% KHSO4 solution and extracted with Et2O (3×)
  4. washThe organic layers were washed with aq. 10% KHSO4 solution and aq. 10% NaCl solution
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. custompurified by flash silica gel column (n-heptane:EtOAc 1:1)

Sources & evidence

ORD record
ord-062b9b235aca4b718b5ab36524a57020
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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