(3-Hydroxy-3-methyloctyl)(triphenyl)phosphonium iodide → ethyl 2-[(2-{(1R,2S,5R)-2-(acetyloxy)-5-[(1E)-4-hydroxy-4-methyl-1-nonenyl]cyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylate

HRID 1888314Notes

Reaction equation

HRID 1888314 reaction equation
[I-].[OH:2][C:3]([CH3:30])([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[C:36]([O:39][C@H:40]1[CH2:44][CH2:43][C@H:42]([CH:45]=O)[C@H:41]1[CH2:47][CH2:48][S:49][C:50]1[S:51][CH:52]=[C:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[N:54]=1)(=[O:38])[CH3:37]>O1CCCC1>[C:36]([O:39][C@H:40]1[CH2:44][CH2:43][C@H:42](/[CH:45]=[CH:5]/[CH2:4][C:3]([OH:2])([CH3:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:41]1[CH2:47][CH2:48][S:49][C:50]1[S:51][CH:52]=[C:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[N:54]=1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 86054281(3-Hydroxy-3-methyloctyl)(triphenyl)phosphonium iodideHCID 86634273Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-formylcyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylateHCID 178418339Butyllithium

Product 1

HCID 66858309ethyl 2-[(2-{(1R,2S,5R)-2-(acetyloxy)-5-[(1E)-4-hydroxy-4-methyl-1-nonenyl]cyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylateYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3-hydroxy-3-methyloctyl)(triphenyl)phosphonium iodide (800 mg) in anhydrous tetrahydrofuran (9.00 mL) was added n-butyllithium (1.60M in hexane, 1.90 mL) at room temperature and the solution was stirred for 1 Hour. To the solution was added a solution of the compound 49 (349 mg) in anhydrous tetrahydrofuran (6.00 mL) was slowly added at −78° C. and the solution was stirred for 2 Hours. The solution temperature was risen to room temperature. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (178 mg) having the following physical data.

Workup

  1. additionwas slowly added at −78° C.
  2. stirringthe solution was stirred for 2 Hours
  3. customwas risen to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-3e9d421a4a4b4158ab3cce3b0ae3657a
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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