Triphenylphosphine → S-[1-(4,5-Dihydro-2-thiazolyl)-3-azetidinyl] ethanethioate

HRID 1489836Notes

Reaction equation

HRID 1489836 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[CH:33]1[CH2:36][N:35]([C:37]2[S:38][CH2:39][CH2:40][N:41]=2)[CH2:34]1.[C:42]([OH:45])(=[S:44])[CH3:43]>O1CCCC1>[C:42]([S:44][CH:33]1[CH2:36][N:35]([C:37]2[S:38][CH2:39][CH2:40][N:41]=2)[CH2:34]1)(=[O:45])[CH3:43]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 109865151-(4,5-Dihydrothiazol-2-yl)azetidin-3-olHCID 178418634HCID 178418634, compound

Product 1

HCID 11790619S-[1-(4,5-Dihydro-2-thiazolyl)-3-azetidinyl] ethanethioateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture solution of triphenylphosphine and diethyl azodicarboxylate in 10 ml of tetrahydrofuran was added a mixture of 119 mg of Compound (3) and thioacetic acid under ice-cooling, and the reaction mixture was stirred for 1 hour at the same condition, then for 1 hour at room temperature. After the reaction solvent was removed under reduced pressure, the resulting residue was purified by silica gel column chromatography (chloroform: ethanol=1:1) to give 107 mg (65%) of 3-acetylthio-1-(thiazolin-2-yl)azetidine [Compound (4)].

Workup

  1. temperaturecooling
  2. waitfor 1 hour at room temperature
  3. customAfter the reaction solvent was removed under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (chloroform: ethanol=1:1)

Sources & evidence

ORD record
ord-cc504ecae3bf47d5a1af73328a1457c4
Source dataset
uspto-grants-1997_10
Patent number
US05679790

Reaction notes

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