Methyl iodide → HCID 57947389, compound

HRID 409855Notes

Reaction equation

HRID 409855 reaction equation
[H-].[Na+].[N:3]([CH2:6][C@H:7]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N+:4]=[N-:5].[CH3:25]I>CN(C=O)C>[N:3]([CH2:6][C@H:7]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[CH2:8][O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[N+:4]=[N-:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57947555HCID 57947555, compound

Product 1

HCID 57947389HCID 57947389, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution NaH (0.29 g, 7.35 mmol) in DMF (10 mL) was added a solution of (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 4.9 mmol) in DMF (10.0 mL). The mixture was stirred at RT for 30 min followed by addition of MeI (1.0 mL, 9.8 mmol). The resulting mixture was stirred for another 2 h. LCMS indicated the completion of the reaction. The mixture was quenched with saturated NH4Cl solution and extracted with EtOAc (200 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-yl(methyl)carbamate (1.8 g, crude), which was used without purification.

Workup

  1. stirringThe resulting mixture was stirred for another 2 h
  2. customthe completion of the reaction
  3. customThe mixture was quenched with saturated NH4Cl solution
  4. extractionextracted with EtOAc (200 mL×2)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae2444c0982e480a910b74576e459a94
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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