Phosphate → HCID 11201113, compound

HRID 1888302Notes

Reaction equation

HRID 1888302 reaction equation
[OH:1][C@@H:2]([CH2:24][C@@H:25]([CH3:30])[CH2:26][CH2:27][CH2:28][CH3:29])/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[C@@H:6]1[CH2:11][CH2:12][S:13][C:14]1[S:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[N:18]=1.P([O-])([O-])([O-])=O>CS(C)=O.C(OCC)(=O)C>[OH:1][C@@H:2]([CH2:24][C@@H:25]([CH3:30])[CH2:26][CH2:27][CH2:28][CH3:29])/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[C@@H:6]1[CH2:11][CH2:12][S:13][C:14]1[S:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=1

Participants

5

Reactant 2

HCID 1061PhosphateHCID 66858273ethyl 2-[(2-{(1R,2R)-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylate

Product 1

HCID 11201113HCID 11201113, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound 29 (142 mg) in dimethylsulfoxide (7.00 mL)/phosphate buffer (7.00 mL) was added esterase from porcine liver (0.850 mL) and the solution was stirred at room temperature for 4 hours. The reaction solution was diluted with ethyl acetate and washed with an aqueous saturated ammonium sulfate solution, 1N hydrochloric acid, water and brine. The reaction solution was dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate), to give the title compound (88.0 mg) having the following physical data.

Workup

  1. washwashed with an aqueous saturated ammonium sulfate solution, 1N hydrochloric acid, water and brine
  2. dry with materialThe reaction solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-918df66f60d9407c95c0eaa312e929d2
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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