Water → HCID 86665989, compound

HRID 1752139Notes

Reaction equation

HRID 1752139 reaction equation
[CH2:1]([O:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH3:2].[H-].[Na+].[CH3:14]I.O>CN(C=O)C>[CH2:1]([O:3][N:4]([CH3:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23210943HCID 23210943, compound

Product 1

HCID 86665989HCID 86665989, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of tert-butyl ethoxycarbamate (XCIII, 2.48 g, 15.38 mmol) in DMF (10 mL) was added dropwise to the suspension of 60% sodium hydride (0.66 g, 16.92 mmol) in DMF (5 mL) at 0° C. After 30 min. methyl iodide (1.95 mL, 31.32 mmol) in DMF (10 mL) was added, and the reaction mixture was stirred at room temperature for 24 h. Water (100 mL) was added and the product was extracted with ethyl acetate (3×50 mL), dried over Na2SO4, and concentrated in vacuo to yield tert-butyl ethoxy(methyl)carbamate (XCIV, 2.34 g, 87%). 400 MHz 1H NMR (DMSO-d6, ppm) 3.81 (2H, q, J=7.0 Hz), 3.00 (3H, s), 1.41 (9H, s), 1.12 (3H, t, J=7.0 Hz).

Workup

  1. extractionthe product was extracted with ethyl acetate (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fad20be6ffb4109afaa123b4aa2b89b
Source dataset
uspto-grants-2015_10
Patent number
US09162992B2

Reaction notes

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