Cesium carbonate → (S)-tert-Butyl((3-(2-(4-formylphenoxy)ethoxy)phenyl)(phenyl)methyl)carbamate

HRID 874837Notes

Reaction equation

HRID 874837 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]=[O:40])=[CH:35][CH:34]=1>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([CH:39]=[O:40])=[CH:35][CH:34]=2)[CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2627064-(2-Bromoethoxy)BenzaldehydeHCID 90209372(S)-tert-butyl((3-hydroxyphenyl)(phenyl)methyl)carbamate

Product 1

HCID 90210008(S)-tert-Butyl((3-(2-(4-formylphenoxy)ethoxy)phenyl)(phenyl)methyl)carbamateYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (S)-tert-butyl((3-hydroxyphenyl)(phenyl)methyl)-carbamate (1.76 g, 5.9 mmol) in DMF (10 mL) was added cesium carbonate (4.0 g, 12.0 mmol). The reaction mixture was then stirred at room temperature for 20 minutes. 4-(2-Bromoethoxy)benzenecarboxaldehyde (1.35 g, 5.9 mmol) was added and the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine (×3), dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0 to 50% ethyl acetate/iso-hexane to afford the title compound (1.6 g, 61%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 5 hours
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic extracts were washed with brine (×3)
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated at reduced pressure
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 0 to 50% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-36ff6d4bbe6f40c893f2f0d292bd89c4
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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