Triphenylphosphine → HCID 131719456, compound

HRID 1957386Notes

Reaction equation

HRID 1957386 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][S:6][C:5]([S:8][CH3:9])=[N:4]1.[C:10]([OH:13])(=S)C.[C:14]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:10][O:13][C@:3]1([CH2:2][O:1][CH3:14])[CH2:7][S:6][C:5]([S:8][CH3:9])=[N:4]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22862349(4R)-4,5-Dihydro-2-(methylthio)-4-thiazolemethanolHCID 178418634HCID 178418634, compound

Product 1

HCID 131719456HCID 131719456, compoundYield 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-4952f7aa8a8c4b8798916ee51476679c
Source dataset
uspto-grants-1998_07
Patent number
US05783703

Reaction notes

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