Triphenylphosphine → HCID 11325272, compound

HRID 1452563Notes

Reaction equation

HRID 1452563 reaction equation
[O:1]=[S:2]1(=[O:25])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]=[N+]=[N-])[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.O>[O:25]=[S:2]1(=[O:1])[CH2:3][CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH2:20])[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 11222326HCID 11222326, compound2×

Product 1

HCID 11325272HCID 11325272, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(azidomethyl) oxazolidin-2-one (Intermediate 2) (3 g, 8.2 mmol) was dissolved in acetonitrile/water (10:1, 50 ml). Triphenylphosphine (2.6 g, 9.9 mmol) was added and the resulting mixture was stirred over night with evolution of nitrogen. The reaction mixture was applied onto a silica gel column and eluted with acetonitrile/water (15:1 to 5:1) to give the title compound (2.67 g).

Workup

  1. washeluted with acetonitrile/water (15:1 to 5:1)

Sources & evidence

ORD record
ord-7e1636bac1da4ec799a31f7f914a08a8
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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