Methyl iodide → HCID 69038045, compound

HRID 2223244Notes

Reaction equation

HRID 2223244 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:14](=[O:15])[N:13]([CH3:21])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate

Product 1

HCID 69038045HCID 69038045, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.94 g (3.38 mmol) (S)-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester dissolved in 20 ml of tetrahydrofurane at −78° C., 3.4 ml of lithium bis(trimethylsilyl)amide (1N solution in tetrahydrofurane) were added. The reaction mixture was stirred for 30 minutes at −78° C. and was allowed to reach room temperature. Iodomethane was slowly added and stirring was continued for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with saturated NaHSO4 solution and separated. The aqueous phase was extracted twice with ethyl acetate (2×50 ml). The combined organic layers were washed with water (2×100 ml), with brine (1×100 ml), dried over MgSO4, filtered and evaporated. The residue was purified by chromatography (heptane/ethyl acetate=7:3) to yield 0.855 g (87%) of the product as a light yellow solid.

Workup

  1. customto reach room temperature
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. washwashed with saturated NaHSO4 solution
  5. customseparated
  6. extractionThe aqueous phase was extracted twice with ethyl acetate (2×50 ml)
  7. washThe combined organic layers were washed with water (2×100 ml), with brine (1×100 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by chromatography (heptane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-b5cf3b3c80404d4c8c52f0705bf3bfeb
Source dataset
uspto-grants-2008_05
Patent number
US07375099B2

Reaction notes

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