Water → Ethyl 2-(1-azetidinylsulfinyl)-2-methylpropanoate

HRID 1802384Notes

Reaction equation

HRID 1802384 reaction equation
ClCl.[CH2:3]([O:5][C:6](=[O:14])[C:7]([S:10]C(=O)C)([CH3:9])[CH3:8])[CH3:4].C([N:18]([CH2:22][CH3:23])[CH:19](C)C)(C)C.N1CCC1.[OH2:28]>C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:14])[C:7]([S:10]([N:18]1[CH2:19][CH2:23][CH2:22]1)=[O:28])([CH3:8])[CH3:9])[CH3:4]

Participants

7

Reactant 5

HCID 962WaterHCID 10422AzetidineHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 57937863Ethyl 2-(acetylthio)-2-methylpropanoate

Product 1

HCID 59267857Ethyl 2-(1-azetidinylsulfinyl)-2-methylpropanoateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chlorine gas is bubbled through a biphasic mixture of 5 g (26 mmol) of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester in DCM (50 mL) and water (50 mL) at 10° C. for 10 min. After this time, the organic phase is separated, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude sulfinyl chloride is re-dissolved in DCM (50 mL) and N,N-diisopropylethylamine (4.58 mL, 26 mmol) and azetidine (1.5 g, 26 mmol) are introduced. The reaction is stirred at room temperature for 1 h and then concentrated under reduced pressure. The residue is purified by column chromatography (silica, eluent heptanes, ethyl acetate) provides 4.62 g of 2-(azetidine-1-sulfinyl)-2-methyl-propionic acid ethyl ester. Yield: 80%, ES-MS: m/z 220 [M+H].

Workup

  1. customAfter this time, the organic phase is separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe crude sulfinyl chloride is re-dissolved in DCM (50 mL)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography (silica, eluent heptanes, ethyl acetate)

Sources & evidence

ORD record
ord-4626c7fe354c4f2dac4b058382606634
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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