Triethylamine → HCID 69198458, compound

HRID 2377663Notes

Reaction equation

HRID 2377663 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH:10]([CH2:19][CH2:20]Cl)[C:9]2=[O:22])=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=1.C(N(CC)CC)C>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH:10]([CH2:19][CH2:20][S:30][C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)[C:9]2=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 677894-Fluorothiophenol2×HCID 691989143-(2-Chloroethyl)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)azetidin-2-one

Product 1

HCID 69198458HCID 69198458, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of 1-(4-fluorophenyl)-3-(2-chloroethyl)-4-(4-hydroxyphenyl)azetidin-2-one (Method 12; 0.750 g, 2.35 mmol) in MeCN (10 ml) was added 4-fluorothiophenol (0.500 ml, 4.60 mmol) and triethylamine (0.500 ml, 3.59 mmol) at room temperature. After 20 hours there were still start materiel left (approximately 20%, LC/MS) and more 4-fluorothiophenol (0.250 ml, 2.30 mmol) and triethylamine (0.170 ml, 1.22 mmol) were added. After 24 hours, the solvent was removed under reduced pressure and the residue was partitioned between water (20 ml) and EtOAc (20 ml). The organic layer was washed with brine (5 ml), dried over magnesium sulphate and concentrated. The residue was refluxed in heptane for 30 minutes before the title compound was filtered off as a grey solid (0.946 g; 98%). NMR (CD3OD, 400 MHz) 2.00-2.20 (m, 2H), 3.05 (t, 2H), 3.25 (dt, 1H), 4.75 (d, 1H), 6.75-6.80 (m, 2H), 6.90-7.05 (m, 4H), 7.15-7.40 (m, 6H); m/z: 412.0.

Workup

  1. additionwere added
  2. waitAfter 24 hours
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was partitioned between water (20 ml) and EtOAc (20 ml)
  5. washThe organic layer was washed with brine (5 ml)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. temperatureThe residue was refluxed in heptane for 30 minutes before the title compound
  9. filtrationwas filtered off as a grey solid (0.946 g; 98%)

Sources & evidence

ORD record
ord-0463e96b72114c59b2b51be2429f734f
Source dataset
uspto-grants-2008_12
Patent number
US07470678B2

Reaction notes

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