Sulfuric Acid → Lithium 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate

HRID 388908Notes

Reaction equation

HRID 388908 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]([CH:11]1[CH2:14][O:13][CH2:12]1)[C:7]([O:9]C)=[O:8])=[O:4].O.[OH-].[Li+:17].S(=O)(=O)(O)O.[Li+].[OH-]>C1COCC1.O.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O.CC(=O)OCC>[CH3:1][O:2][C:3]([NH:5][CH:6]([CH:11]1[CH2:12][O:13][CH2:14]1)[C:7]([O-:9])=[O:8])=[O:4].[Li+:17]

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 66648610Methyl 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate

Product 1

HCID 59264533Lithium 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetateYield 114.6%

Reagents, catalysts & solvents 4

HCID 61578Diammonium molybdateCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To methyl 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate (50 mg, 0.246 mmol) in THF (2 mL) and water (0.5 mL) was added lithium hydroxide monohydrate (10.33 mg, 0.246 mmol). The resultant solution was allowed to stir overnight at ambient temperature. TLC (1:1 EA/Hex; Hanessian stain [1 g Ce(NH4)2SO4, 6 g ammonium molybdate, 6 ml sulfuric acid, and 100 ml water]) indicated ˜10% starting material remaining. Added an additional 3 mg LiOH and allowed to stir overnight at which time TLC showed no starting material remaining. Concentrated in vacuo and placed on high vac overnight providing 55 mg lithium 2-(methoxycarbonylamino)-2-(oxetan-3-yl)acetate as a colorless solid. 1H NMR (500 MHz, MeOD) δ ppm 3.39-3.47 (m, 1H) 3.67 (s, 3 H) 4.28 (d, J=7.93 Hz, 1H) 4.64 (t, J=6.26 Hz, 1H) 4.68 (t, J=7.02 Hz, 1H) 4.73 (d, J=7.63 Hz, 2H).

Workup

  1. stirringto stir overnight at which time TLC
  2. concentrationConcentrated in vacuo
  3. waitplaced on high vac overnight

Sources & evidence

ORD record
ord-499e169da05f4fbeb8da691f40fc7d72
Source dataset
uspto-grants-2013_02
Patent number
US08377980B2

Reaction notes

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