Cesium carbonate → Tert-butyl 4-(3-(diethoxyphosphoryl)propoxy)phenethylcarbamate

HRID 2204996Notes

Reaction equation

HRID 2204996 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][CH2:26][CH2:27][P:28](=[O:35])([O:32][CH2:33][CH3:34])[O:29][CH2:30][CH3:31]>CN(C=O)C>[CH2:33]([O:32][P:28]([CH2:27][CH2:26][CH2:25][O:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[CH:4][CH:3]=1)([O:29][CH2:30][CH3:31])=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 283500Diethyl (3-bromopropyl)phosphonateHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate2×

Product 1

HCID 86678287Tert-butyl 4-(3-(diethoxyphosphoryl)propoxy)phenethylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-hydroxyphenethylcarbamate (1 eq) in DMF (0.17 M) was added cesium carbonate (5 eq). The resulting mixture was stirred at room temperature for 30 minutes, then diethyl 3-bromopropylphosphonate (1.2 eq) was added into the reaction mixture. The resulting mixture was stirred at room temperature for another 4 hours until tert-butyl 4-hydroxyphenethylcarbamate was consumed. The mixture was then diluted with ethyl acetate, and washed with 5% citric acid three times, saturated NaHCO3 solution, water and brine. The organic layer was then dried over anhydrous Na2SO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 80-100% EtOAc/Hex to give the product as a colorless oil.

Workup

  1. customwas consumed
  2. additionThe mixture was then diluted with ethyl acetate
  3. washwashed with 5% citric acid three times, saturated NaHCO3 solution, water and brine
  4. dry with materialThe organic layer was then dried over anhydrous Na2SO4
  5. concentrationconcentrated en vaccuo
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-6cbbe24ed76f4a27a327ad4a43c1aa55
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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