Sodium Thiosulfate → 4-[N-dodecyl-N-[2-[4-(3oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester

HRID 1383913Notes

Reaction equation

HRID 1383913 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[CH2:23]([N:35]([CH2:53][CH2:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH2:36][CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH:47]([OH:52])[C:48]([F:51])([F:50])[F:49])=[CH:41][CH:40]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH2:23]([N:35]([CH2:53][CH2:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH2:36][CH2:37][O:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:45][CH2:46][C:47](=[O:52])[C:48]([F:49])([F:50])[F:51])=[CH:43][CH:44]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 867571234-[N-Dodecyl-N-2-[4-[3-hydroxy-4,4,4-trifluorobutyl]phenoxy]ethylamino]butanoic acid, ethyl ester

Product 1

HCID 867571224-[N-dodecyl-N-[2-[4-(3oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl esterYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

A suspension of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane, 1.7 g, 4.0 mmol) in dichloromethane (20 ml) was treated with 4-[N-dodecyl-N-2-[4-[4,4,4-trifluoro-3-hydroxybutyl]phenoxy]ethylamino]butanoic acid, ethyl ester (430 mg, 0.79 mmol) dissolved in dichloromethane (5 ml). The mixture was stirred at 22° C. for 4 h, poured into a saturated aqueous sodium bicarbonate and sodium thiosulfate (100 ml) and extracted with ethyl acetate (2×100 ml). The combined oganic layers were washed with sat. sodium bicarbonate (2×60 ml), brine (60 ml), dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane/ethyl acetate 2:1 to 1.5:1) to afford the title compound (333 mg, 77%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe combined oganic layers were washed with sat. sodium bicarbonate (2×60 ml), brine (60 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (hexane/ethyl acetate 2:1 to 1.5:1)

Sources & evidence

ORD record
ord-bc487d13d38d424896bb7c822dce946c
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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