Acetic Acid → HCID 88352063, compound

HRID 2697Notes

Reaction equation

HRID 2697 reaction equation
[Li+].[CH2:2]([O:4][P:5]([O:19][CH2:20][CH3:21])([CH:7]([S:15]([O-:18])(=[O:17])=[O:16])[CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:6])[CH3:3].C([Li:26])CCC.C(O)(=[O:29])C>O1CCCC1>[Li+:26].[CH2:2]([O:4][P:5]([O:19][CH2:20][CH3:21])([C:7]([OH:29])([S:15]([O-:18])(=[O:17])=[O:16])[CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 88352138HCID 88352138, compoundHCID 178418339Butyllithium

Product 1

HCID 88352063HCID 88352063, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 3.29 g (0.01 mole) of 1-diethoxyphosphinyl-2-(3-pyridinyl)ethanesulfonic acid lithium salt (from part I of Example 16) in 50 ml of anhydrous tetrahydrofuran is stirred in a -40° bath under a dry nitrogen atmosphere. To this is added n-butyl lithium (4.4 ml of 2.5M solution in hexanes; 0.011 mole) via syringe over 5 minutes. The reaction mixture is allowed to warm to -15° , and is stirred at this temperature for about one hour. It is then cooled to -78°, and to it is added dropwise a solution of 3.44 g (0.015 mole) of camphorylsulfonyloxaziridine (J. Am. Chem. Soc., 112, 6679(1990)) in 50 ml of anhydrous THF. The reaction mixture is stirred for a few minutes at -78°, and then is placed in an ice/water bath. It is stirred at 0° for 2-10 minutes, and then is again cooled to -78° . The reaction mixture is quenched by addition of 1.2 g (0.02 mole) of acetic acid and the solvents are removed under vacuum on a rotary evaporator. The residue was purified by chromatography on silica gel using chloroform/methanol as eluant, to yield 1-diethoxyphosphinyl-1-hydroxy-2-(3-pyridinyl)ethanesulfonic acid lithium salt.

Workup

  1. temperatureto warm to -15°
  2. stirringis stirred at this temperature for about one hour
  3. temperatureIt is then cooled to -78°
  4. stirringThe reaction mixture is stirred for a few minutes at -78°
  5. customis placed in an ice/water bath
  6. stirringIt is stirred at 0° for 2-10 minutes
  7. temperatureis again cooled to -78°
  8. customthe solvents are removed under vacuum on a rotary evaporator
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c441ac980b3c4b878d770f161b660243
Source dataset
uspto-grants-1998_03
Patent number
US05731299

Reaction notes

Loading…