Chloroform → HCID 131711707, compound

HRID 2052346Notes

Reaction equation

HRID 2052346 reaction equation
CS(O)(=O)=O.[CH:6]([N:9]1[CH2:12][CH:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10]1)([CH3:8])[CH3:7].C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>C(OCC)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[CH:6]([N:9]1[CH2:10][CH:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:12]1)([CH3:8])[CH3:7].[CH:6]([N:9]1[CH2:10][CH:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:12]1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 444266Maleic AcidHCID 516892Sodium BicarbonateHCID 86736791HCID 86736791, compound

Product 1

HCID 131711707HCID 131711707, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

Add 1.0 mole of 1-isopropyl-3-methanesulfonyloxyazetidine methanesulfonate and chloroform to aqueous 1.1 M sodium bicarbonate with agitation. Saturate the aqueous phase with sodium chloride, filter and wash the solid with chloroform. Separate the phases of the combined filtrate and washes and extract the aqueous layer several times with chloroform. Dry the combined extract over sodium sulfate and filter. Add the filtrate to a solution of 1.0 mole of maleic acid in diethyl ether and warm the mixture to about 30° C. Isolate the product, 1-isopropyl-3-methanesulfonyloxyazetidine hemimaleate, by filtration and air-dry. This salt has the ratio of 1 mole 1-isopropyl-3-methanesulfonyloxyazetidine to 1 mole of maleic acid and melts within the range 115°-121° C.

Workup

  1. concentrationSaturate the aqueous phase with sodium chloride
  2. filtrationfilter
  3. washwash the solid with chloroform
  4. customSeparate the phases of the combined filtrate and washes
  5. extractionextract the aqueous layer several times with chloroform
  6. customDry the
  7. extractioncombined extract over sodium sulfate
  8. filtrationfilter

Sources & evidence

ORD record
ord-ab2a831006df4850b2e81ba128588b3b
Source dataset
uspto-grants-1980_01
Patent number
US04183923

Reaction notes

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