Cesium carbonate → HCID 69201094, compound

HRID 2377664Notes

Reaction equation

HRID 2377664 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][S:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:9]2=[O:29])=[CH:4][CH:3]=1.Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:16][CH:17]=3)[CH:10]([CH2:19][CH2:20][S:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C:9]2=[O:29])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 69198458HCID 69198458, compound

Product 1

HCID 69201094HCID 69201094, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1-(4-fluorophenyl)-3-[2-(4-fluorophenylthio)ethyl]-4-(4-hydroxyphenyl)azetidin-2-one (Method 13; 0.800 g, 1.944 mmol), t-butyl bromoacetate (0.32 ml, 2.17 mmol) and caesium carbonate (0.700 g, 2.15 mmol) in MeCN (15 ml) was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between water (20 ml) and DCM (20 ml). The water layer was extracted once more with DCM (10 ml) and the combined organic layers were washed with brine, dried over magnesium sulphate and concentrated. The residue was purified by flash chromatography using heptane:EtOAc (4:1) as eluent The title compound was obtained as a colourless oil (0.884 g; 87%). NMR (400 MHz) 1.45 (s, 9H), 2.00-2.30 (m, 2H), 2.90-3.10 (m, 2H), 3.15-3.25 (m, 1H), 4.50 (s, 2H), 4.60 (d, 1H), 6.85-7.00 (m, 6H), 7.15-7.35 (m, 6H); m/z: 526.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water (20 ml) and DCM (20 ml)
  3. extractionThe water layer was extracted once more with DCM (10 ml)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. customwas obtained as a colourless oil (0.884 g; 87%)

Sources & evidence

ORD record
ord-29c1d37d59bd4a73b56ef7c160ed07b9
Source dataset
uspto-grants-2008_12
Patent number
US07470678B2

Reaction notes

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