Pyrrolidine → 3,3,3-Trifluoro-2-hydroxy-2-methyl-N-[4-(1-pyrrolidinylsulfonyl)phenyl]propanamide

HRID 1938168Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]([OH:18])([CH3:17])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](F)(=[O:15])=[O:14])=[CH:9][CH:8]=1)=[O:5].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.N1(C2C=CN=CC=2)CCCC1>C(#N)C.O>[F:1][C:2]([F:20])([F:19])[C:3]([OH:18])([CH3:17])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)=[O:5]

Participants

Conditions

Temperature: 22 °C

Procedure

A solution of 3,3,3-trifluoro-N-(4-flurosulfonylphenyl)-2-hydroxy-2-methylpropanamide (0.25 g), pyrrolidine (0.28 g), and 4-pyrrolidinopyridine (12 mg) in dry acetonitrile (3 ml) was heated at reflux for 24 hours. After cooling to 22° C., the reaction mixture was diluted with water (25 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with 1N HCl, brine, dried (Na2SO4) and evaporated to give an oil which crystallized upon suspension in hexane to yield the title compound as an off-white crystalline solid (0.27 g); mp 183°-186° C.; MS: m/z=367(M+1); NMR: 1.59 (s,3), 1.62 (m,4), 3.12 (m,4), 7.56 (s,1), 7.75-7.77 (m,2), 8.00-8.03 (m,2), 10.40 (s,1). Analysis for C14H17F3N2O4S: Calculated: C, 45.89; H, 4.68; N, 7.65; Found: C, 45.98; H, 4.76; N, 7.56.

Workup

temperatureat reflux for 24 hours
extractionextracted with ethyl acetate (3×15 ml)
washThe combined organic extracts were washed with 1N HCl, brine
dry with materialdried (Na2SO4)
customevaporated
customto give an oil which
customcrystallized upon suspension in hexane

Sources & evidence

ORD record: ord-32d74badd89e4e6bbd9bd83ff880776a
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693639

Reaction notes

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