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Cesium carbonate → HCID 68867360, compound

HRID 1985180
Notes
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Reaction equation

HRID 1985180 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:23][C:24]1[CH:52]=[CH:51][C:27]([CH2:28][N:29]2[CH2:33][CH:32]([CH2:34][CH2:35]OS(C3C=CC(C)=CC=3)(=O)=O)[N:31]([CH2:47][CH2:48][CH3:49])[C:30]2=[O:50])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:35][CH2:34][CH:32]2[CH2:33][N:29]([CH2:28][C:27]3[CH:51]=[CH:52][C:24]([CH3:23])=[CH:25][CH:26]=3)[C:30](=[O:50])[N:31]2[CH2:47][CH2:48][CH3:49])=[CH:9][CH:8]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionateHCID 57719317HCID 57719317, compound

Product 1

HCID 68867360HCID 68867360, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-(4-hydroxy-phenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (0.80 g, 2.66 mmol), toluene-4-sulfonic acid 2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethyl ester (1.26 g, 2.93 mmol) and Cs2CO3 (1.04 g, 3.19 mmol) in DMF (40 mL) is heated to 55° C. under N2 for 17 h. The reaction is cooled and quenched with 1 N HCl (20 mL) and worked up extractively with Et2O and water. The organic layer is dried and the solvent removed to afford crude product that is purified by flash chromatography using 7:1 hexanes:acetone to afford 1.02 g (68%) 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester. The diasteriomeric products were separated by chiral HPLC (90:10 heptane:IPA, 280 mL/min, 220 nm,) to give products in >99% de. Rf=0.49 (1:1 acetone:hexanes). 1H NMR. MS (ES+) Calc'd for C34H43N2O5 (M+1) 559. Found m/z 559 (100%).

Workup

  1. temperatureThe reaction is cooled
  2. customquenched with 1 N HCl (20 mL)
  3. customThe organic layer is dried
  4. customthe solvent removed
  5. customto afford crude product that
  6. customis purified by flash chromatography

Sources & evidence

ORD record
ord-4e5d4890e1904f229732685ea40ba951
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07544812B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes