Triphenylphosphine → HCID 86678896, compound

HRID 1620736Notes

Reaction equation

HRID 1620736 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:4]1[CH2:3][CH2:2][N:6]2[C:5]=1[CH2:9][S:8][C:7]2=[O:10]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 66880968DIAD tolueneHCID 178518158HCID 178518158, compound

Product 1

HCID 86678896HCID 86678896, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-[(2-hydroxyethyl)amino]-1,3-thiazol-2(5H)-one (641 mg) and triphenylphosphine (1570 mg) in THF (10 mL) was added 1.9M diisopropyl azodicarboxylate toluene solution (3.16 mL) at room temperature. The reaction mixture was stirred overnight at 40° C. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (260 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-091e914b51b84a5186dbb9b0a04ad2c4
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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