Triphenylphosphine → HCID 117873614, compound

HRID 517392Notes

Reaction equation

HRID 517392 reaction equation
[F:1][C:2]([F:35])([CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)/[CH:3]=[CH:4]/[C@H:5]1[C@H:9]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH2:8][C@H:7](O)[C@@H:6]1[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25].C1C=C(SSC2N=CC=CC=2)N=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]([F:35])([CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:6]2[C@@H:7]([O:25][C:24](=[O:26])[CH2:23][CH2:22][CH2:21][CH:20]=[CH:19][CH2:18]2)[CH2:8][C@H:9]1[O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 117875117HCID 117875117, compound

Product 1

HCID 117873614HCID 117873614, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of (Z)-7-((1R,2R,3R,5S)-2-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoic acid (145.0 g from Example 32) in xylene (2 L) was treated with 2,2′-dipyridyl disulfide (90.0 g, 0.41 mol.) and triphenylphosphine (123.0 g, 0.47 mol.). This mixture was then stirred for 1 hr at room temperature under an atmosphere of nitrogen. The resulting mixture was heated to 80° C. for 18 hr (TLC monitoring), followed by removal of xylene under reduced pressure. The residue was diluted with saturated aqueous solution of sodium bicarbonate (1.6 L) and extracted with ethyl acetate (1.6 L). The organic layer is dried over magnesium sulfate and concentrated under reduced pressure to give 322.0 g of crude product. The crude product was purified by column chromatography providing 26.0 g of the title compound (48% yield, 3 steps).

Workup

  1. temperatureThe resulting mixture was heated to 80° C. for 18 hr (TLC monitoring)
  2. customfollowed by removal of xylene under reduced pressure
  3. additionThe residue was diluted with saturated aqueous solution of sodium bicarbonate (1.6 L)
  4. extractionextracted with ethyl acetate (1.6 L)
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give 322.0 g of crude product
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-5e96f7de3e1e44babbe7265cbbc0b2ae
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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