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

HRID 2258112Notes

Reaction equation

HRID 2258112 reaction equation
O[CH:2]1[CH2:5][N:4]([C:6]2[S:7][CH2:8][CH2:9][N:10]=2)[CH2:3]1.[C:11]([OH:14])(=[S:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:11]([S:13][CH:2]1[CH2:5][N:4]([C:6]2[S:7][CH2:8][CH2:9][N:10]=2)[CH2:3]1)(=[O:14])[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 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

There were added 119 mg of 3-hydroxy-1-(1,3-thiazolin-2-yl)azetidine (6) and two molar equivalents of thioacetic acid, while cooled with ice, to 10 ml of tetrahydrofuran solution containing two molar equivalents of triphenylphosphine and two molar equivalents of diethylazodicarboxylate, and the resultant solution was stirred for one hour at the same temperature, and for further one hour at a room temperature. The solvent of the reaction liquid was evaporated in a vacuum, and the obtained residue was subjected to silica gel column chromatography (eluent: chloroform-ethanol), and, thus, there was obtained 107 mg (yield: 65%) of 3-acetylthio-1-(1,3-thiazolin-2-yl)azetidine (7).

Workup

  1. customThe solvent of the reaction liquid
  2. customwas evaporated in a vacuum

Sources & evidence

ORD record
ord-75aa402e56ea4304993e1a1a5a7b8475
Source dataset
uspto-grants-1997_08
Patent number
US05659043

Reaction notes

Loading…