Acetonitrile → 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid

HRID 1796133

Reaction equation

[CH2:1]=[C:2]([CH2:6][C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8])[C:3]([OH:5])=[O:4].[CH2:15]([S:19]([OH:21])=[O:20])[CH:16]([CH3:18])[CH3:17].C(#N)C>C1(C)C=CC=CC=1>[CH3:17][CH:16]([CH3:18])[CH2:15][S:19]([CH2:1][CH:2]([CH2:6][C:7]([N:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)=[O:8])[C:3]([OH:5])=[O:4])(=[O:21])=[O:20]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 2-Methylene-4-morpholin-4-yl-4-oxo-butyric acid (3.98 g, 20 mmol) and isobutyl-sulphinic acid (2.44 g, 20 mmol) were suspended in anhydrous toluene (80 mL) and anhydrous acetonitrile (20 mL). This mixture was warmed to 85° C. and stirred vigorously for 4.5 h. The reaction mixture was allowed to cool to room temperature and concentrated under vacuum. The residue was purified by flash chromatography using a 90 g silica gel column eluting with 10% methanol/CH2Cl2. Recovered 3.7 g of product as an oil. Triturated residue with isopropanol (5 mL)/ether (100 mL). Product began to precipitate out. Cooled this to 5° C. for 17 hrs(overnight). Product was collected by filtration, washed with ether and dried under vacuum to give 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid as a white solid (1.8 g).

Workup

temperatureto cool to room temperature
concentrationconcentrated under vacuum
customThe residue was purified by flash chromatography
washeluting with 10% methanol/CH2Cl2
customRecovered 3.7 g of product as an oil
customto precipitate out
temperatureCooled this to 5° C. for 17 hrs(overnight)
filtrationProduct was collected by filtration
washwashed with ether
customdried under vacuum

Sources & evidence

ORD record: ord-01136e723d504499b19315b80684ec11
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030116B2

Linked notes

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