Triphenylphosphine → HCID 21356671, compound

HRID 1167505Notes

Reaction equation

HRID 1167505 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][N:10]=2)[CH2:4]1.O[C:17]1[CH:21]=[CH:20][O:19][N:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:19]1[CH:20]=[CH:21][C:17]([O:1][CH2:2][C@@H:3]2[O:7][C:6](=[O:8])[N:5]([C:9]3[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][N:10]=3)[CH2:4]2)=[N:18]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 21356616HCID 21356616, compoundHCID 178516613HCID 178516613, compound

Product 1

HCID 21356671HCID 21356671, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5(R)-hydroxymethyl-3-(4-bromo-pyrid-2-yl)oxazolidin-2-one (EP 694543; 3.75 g, 13.7 mmol), 3-hydroxyisoxazole (1.28 g, 15.1 mmol) and triphenylphosphine(4.31 g, 16.4 mmol) in anhydrous THF (83 ml), was added dropwise diisopropyl azodicarboxylate(3.20 g, 3.11 ml, 15.8 mmol) and stirred at room temperature for 5h. The solvent was then removed by rotary evaporation and purification by MPLC (Merck 9385 silica, eluting with CH2Cl2) and trituration with diethyl ether gave the title compound as a white solid (2.93 g, 63%)

Workup

  1. customThe solvent was then removed by rotary evaporation and purification by MPLC (Merck 9385 silica, eluting with CH2Cl2) and trituration with diethyl ether

Sources & evidence

ORD record
ord-429381241b20448cb9197b3cf01a8d19
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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