Cyclopropylmethylsulphinic acid → HCID 22054098, compound

HRID 1796134

Reaction equation

HRID 1796134 reaction equation
[CH:1]1([CH2:4][S:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.[CH2:8]=[C:9]([CH2:13][C:14]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:15])[C:10]([OH:12])=[O:11]>C1(C)C=CC=CC=1.C(#N)C>[CH:1]1([CH2:4][S:5]([CH2:8][CH:9]([CH2:13][C:14]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[O:15])[C:10]([OH:12])=[O:11])(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 17937320Cyclopropylmethylsulphinic acidHCID 220540222-Methylene4-morpholin-4-yl-4-oxo-butyric acid

Product 1

HCID 22054098HCID 22054098, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of cyclopropylmethylsulphinic acid (1.8 g, 15 mmol) in anhydrous toluene (45 mL) and anhydrous acetonitrile (9 mL) was added 2-Methylene4-morpholin-4-yl-4-oxo-butyric acid (2.98 g, 15 mmol). The resulting solution was warmed to 85° C. and stirred at this temperature for 4.5 h. The heterogeneous reaction mixture is then allowed to cool to room temperature then concentrated under reduced pressure. The residue is then purified by flash chromatography eluting with 7% methanol in dichloromethane to give 2-Cyclopropylmethanesulfonylmethyl-4-morpholin-4-yl-4-oxo-butyric acid (1.92 g) as viscous oil which was re crystallized from hot ethyl acetate to give a white solid.

Workup

  1. temperatureto cool to room temperature
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue is then purified by flash chromatography
  4. washeluting with 7% methanol in dichloromethane

Sources & evidence

ORD record
ord-eeb3f2e7ab404a5f96dc1a8bc5ff6cc1
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Linked notes

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