Triphenylphosphine → HCID 131733348, compound

HRID 517399Notes

Reaction equation

HRID 517399 reaction equation
[Si:1]([O:8][CH:9]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:10][CH2:11][C@H:12]1[C@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:15][C@H:14](O)[C@@H:13]1[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].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>[Si:1]([O:8][CH:9]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:10][CH2:11][C@@H:12]1[C@@H:13]2[C@@H:14]([O:32][C:31](=[O:33])[CH2:30][CH2:29][CH2:28][CH:27]=[CH:26][CH2:25]2)[CH2:15][C@H:16]1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 131733349HCID 131733349, compound

Product 1

HCID 131733348HCID 131733348, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of (Z)-7-[(1R,2R,3R,5S)-2-(3-(tert-butyldimethyl-silyloxy)decyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (61 g from Example 39) in 250 mL xylene was treated with 2,2′-dipyridyl disulfide (36 g, 0.17 mol) and triphenylphosphine (38 g, 0.43 mol). This mixture was then stirred for 1 hour at room temperature under an atmosphere of nitrogen and the resulting mixture was heated to 80° C. for 18 hours. Then, the xylene was removed under reduced pressure, and the residue was diluted with 200 ml saturated sodium bicarbonate aqueous solution and extracted with 200 ml ethyl acetate twice. The organic layer was dried over anhydrous MgSO4. The solid was filtered off and organic solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield of the title compound was 25 g (75% in 3 steps).

Workup

  1. temperaturethe resulting mixture was heated to 80° C. for 18 hours
  2. customThen, the xylene was removed under reduced pressure
  3. additionthe residue was diluted with 200 ml saturated sodium bicarbonate aqueous solution
  4. extractionextracted with 200 ml ethyl acetate twice
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationThe solid was filtered off
  7. customorganic solvent was evaporated off under vacuum
  8. customThe crude product was purified by chromatography on silica gel using
  9. additiona mixture of hexane and ethyl acetate as a gradient eluent

Sources & evidence

ORD record
ord-207e2d72458d43e2a7ac681285d004c9
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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