Water → HCID 118177283, compound

HRID 1485089Notes

Reaction equation

HRID 1485089 reaction equation
[C:1]([CH2:3][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:5][OH:6])#[N:2].[H-].[Na+].[CH3:17]I.O>O1CCCC1>[C:1]([CH2:3][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][O:6][CH3:17])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 45091943HCID 45091943, compound

Product 1

HCID 118177283HCID 118177283, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution in tetrahydrofuran (10 mL) of the compound (650 mg) obtained in step (1) above, sodium hydride (60% dispersion in mineral oil, 143 mg) was added under cooling with ice. After stirring the mixture at the same temperature for 10 minutes, methyl iodide (603 μL) was added. After stirring the mixture at the same temperature for 30 minutes and then at room temperature for an hour, water was added and extraction was conducted with ethyl acetate. The combined organic layers were passed through a phase separator and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-60:40) to give tert-butyl [(2S)-1-cyano-3-methoxypropan-2-yl]carbamate as a colorless oil (247 mg).

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring the mixture at the same temperature for 30 minutes
  3. waitat room temperature for an hour
  4. extractionextraction
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10-60:40)

Sources & evidence

ORD record
ord-d73eb8a70ebf45c58cb581956ac95cf7
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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