Water → 4-(2-t-Butoxycarbonylaminoethyl)phenoxymethyl phosphonic acid, diethyl ester

HRID 1527Notes

Reaction equation

HRID 1527 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[OH:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:16]([O:18][P:19]([CH2:24]OS(C1C=CC(Cl)=CC=1)(=O)=O)(=[O:23])[O:20][CH2:21][CH3:22])[CH3:17].O>CS(C)=O>[C:5]([O:13][C:11]([NH:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:24][P:19](=[O:23])([O:18][CH2:16][CH3:17])[O:20][CH2:21][CH3:22])=[CH:7][CH:6]=1)=[O:12])([CH3:8])([CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 9974693HCID 9974693, compoundHCID 204361692-(4-Hydroxyphenyl)ethylcarbamic acid

Product 1

HCID 867521914-(2-t-Butoxycarbonylaminoethyl)phenoxymethyl phosphonic acid, diethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 2-(4-hydroxyphenyl)ethylcarbamic acid, t-butyl ester1 (4.0 g, 16.9 mMol) in dry DMSO (37.5 ml) was cooled in an ice-bath and treated with sodium hydride (80% in mineral oil 0.557 g, 1.1 equiv) with stirring under argon according to the method described by Cornforth2. When effervescence ceased a solution of 4-chlorobenzenesulfonyloxymethylphosphonate diethyl ester (6.07 g, 1.05 equiv) in dry DMSO (110 ml) was added and the resulting pale yellow solution stirred at room temperature overnight. The mixture was then poured into water (550 ml) and extracted with diethyl ether/ethyl acetate (1:1, 3×150 ml) and finally ethyl acetate (3×100 ml). The combined extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated to dryness. The resulting oil was purified by chromatography on silica gel with a gradient of 3:2 pentane:ethyl acetate rising to 100% ethyl acetate to give the title compound as a colourless viscous oil.

Workup

  1. additionwas added
  2. stirringthe resulting pale yellow solution stirred at room temperature overnight
  3. extractionextracted with diethyl ether/ethyl acetate (1:1, 3×150 ml) and finally ethyl acetate (3×100 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe resulting oil was purified by chromatography on silica gel with a gradient of 3:2 pentane

Sources & evidence

ORD record
ord-5e96551488e842a0ae7a5944f04ecff0
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Reaction notes

Loading…