Ammonium Chloride → 1429182-36-4

HRID 1850145Notes

Reaction equation

HRID 1850145 reaction equation
CON(C)[C:4](=[O:16])[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:7])[CH3:6].[CH3:18][Li].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O.O>[CH3:7][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])([C:4](=[O:16])[CH3:18])[CH3:6]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 47451638HCID 47451638, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 229737901429182-36-4Yield 67.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 1-(methoxy(methyl)amino)-2-methyl-1-oxopropan-2-ylcarbamate (4.26 g, 17.30 mmol) in THF (100 mL) at −70° C. was added drop wise methyl lithium (32.4 mL, 51.9 mmol). Cold bath was replaced with −40° C. bath and the reaction was stirred for 4 hours. Saturated NH4Cl solution (10 mL) was then added cautiously to quench the reaction. The reaction mixture was then allowed to warm to room temperature, and diluted with EtOAc (100 mL) and water (50 mL). The phases were separated and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organics were then dried (Na2SO4) and concentrated under reduced pressure. The residue was purified via silica gel flash chromatography (10-50% EtOAc-Hexanes) to afford the desired product as a white solid (2.36 g). LCMS m/z 224.2 (M+Na)+, Rt 0.7 min.

Workup

  1. customwas replaced with −40° C.
  2. customto quench
  3. customthe reaction
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  6. dry with materialThe combined organics were then dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via silica gel flash chromatography (10-50% EtOAc-Hexanes)

Sources & evidence

ORD record
ord-7a7ec0cde2554490a2b1a7f4c8e8ec31
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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