Phosphate → {3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid
Reaction equation
C[O:2][C:3](=[O:26])[CH2:4][S:5][CH2:6][CH2:7][CH2:8][S:9][C@H:10]1[C:14](=[O:15])[CH2:13][C@@H:12]([OH:16])[C@@H:11]1/[CH:17]=[CH:18]/[C@@H:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].P([O-])([O-])([O-])=O>CC#N>[OH:16][C@@H:12]1[CH2:13][C:14](=[O:15])[C@H:10]([S:9][CH2:8][CH2:7][CH2:6][S:5][CH2:4][C:3]([OH:26])=[O:2])[C@H:11]1/[CH:17]=[CH:18]/[C@@H:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
Methyl ester 8 (50 mg, 0.124 mmol) was dissolved in CH3CN (10 L) and pH 7.2 phosphate buffer (3.0 mL) was added. The mixture was treated with PLE (400 L, 1.34 mol/L) and stirred for 16 h at 23° C. The reaction mixture was extracted with EtOAc (3×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 100% EtOAc) gave 5.3 mg (11%) of the above titled compound.
Workup
- additionThe mixture was treated with PLE (400 L, 1.34 mol/L)
- extractionThe reaction mixture was extracted with EtOAc (3×)
- washThe combined organics were washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification of the residue by flash column chromatography (silica gel, 100% EtOAc)
Sources & evidence
- ORD record
- ord-42267eb905ab4a9782fdf3f31d52ad85
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06767920B2
Reaction notes
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