Water → Methyl 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]cyclobutylidene]acetate

HRID 1050995Notes

Reaction equation

HRID 1050995 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:11][C:10](=O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1(P(=[CH:33][C:34]([O:36][CH3:37])=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH3:37][O:36][C:34](=[O:35])[CH:33]=[C:10]1[CH2:11][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13])[CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 23374584tert-Butyl 3-oxocyclobutylcarbamate

Product 1

HCID 23374583Methyl 2-[3-[[(1,1-dimethylethoxy)carbonyl]amino]cyclobutylidene]acetateYield 1,450.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (3-oxo-cyclobutyl)-carbamic acid tert-butyl ester (5.6 g, 30 2 mmol) in anhydrous toluene (100 mL) was added methyl (triphenylphosphoranylidene)acetate (10.7 g, 45.4 mmol) and heated to reflux overnight under N2. After cooling to room temperature, the mixture was poured into water and extracted with EA. The organic phase was dried over Na2SO4, concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (eluted with PE:EA=20:1) to give the title compound (7 g, yield 96%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight under N2
  3. extractionextracted with EA
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue, which
  7. customwas purified by column chromatography on silica gel (eluted with PE:EA=20:1)

Sources & evidence

ORD record
ord-12270812d1804ee3aadb417f20cc2b9a
Source dataset
uspto-grants-2016_07
Patent number
US09388148B2

Reaction notes

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