Lithium Chloride → HCID 12073626, compound

HRID 561767Notes

Reaction equation

HRID 561767 reaction equation
[Cl-].[Li+].[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[C:12](=[O:20])[CH2:13]P(=O)(OC)OC.[F:21][C@H:22]1[CH2:26][C@H:25]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[C@H:24]([CH2:34]/[CH:35]=[CH:36]\[CH2:37][CH2:38][CH2:39][C:40]([O:42][CH:43]([CH3:45])[CH3:44])=[O:41])[C@H:23]1[CH:46]=O.OS([O-])(=O)=O.[K+]>C1COCC1.C(N(CC)CC)C>[CH2:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:3][CH:4]1[C:12](=[O:20])/[CH:13]=[CH:46]/[C@H:23]1[C@@H:22]([F:21])[CH2:26][C@H:25]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[C@@H:24]1[CH2:34]/[CH:35]=[CH:36]\[CH2:37][CH2:38][CH2:39][C:40]([O:42][CH:43]([CH3:45])[CH3:44])=[O:41]

Participants

7

Reactant 4

HCID 433294Lithium ChlorideHCID 516920Potassium bisulfateHCID 12073625HCID 12073625, compoundHCID 14560275HCID 14560275, compound

Product 1

HCID 12073626HCID 12073626, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring mixture consisting of lithium chloride (3.75 g, 88.5 mmol) and triethylamine (4.86 mL) in THF (350 mL) cooled to 0° C. and stirred for 5 minutes at that temperature was added a solution consisting of dimethyl 2-(2,3-dihydro-1H-inden-2-yl)-2-oxoethylphosphonate (8.61 g) in THF (100 mL). The reaction mixture was stirred for 5 minutes and a solution consisting of (Z)-isopropyl 7-((1R,2S,3S,5S)-3-fluoro-2-formyl-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (prepared in Step G, 10.31 g) in THF was added slowly. The reaction mixture was stirred as it was allowed to warm to room temperature overnight. The reaction mixture was subsequently acidified with 5% KHSO4, extracted with DCM, and the organic layers were washed twice with brine. After drying over sodium sulfate, filtration, and solvent removal under reduced pressure, the crude product was purified on silica gel. Elution with hexanes-ethyl acetate (9:1) afforded the title intermediate (13.4 g, 94%).

Workup

  1. additionwas added a solution
  2. stirringThe reaction mixture was stirred for 5 minutes
  3. additionwas added slowly
  4. stirringThe reaction mixture was stirred as it
  5. temperatureto warm to room temperature overnight
  6. extractionextracted with DCM
  7. washthe organic layers were washed twice with brine
  8. dry with materialAfter drying over sodium sulfate, filtration, and solvent removal under reduced pressure
  9. customthe crude product was purified on silica gel
  10. washElution with hexanes-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-e8659c42cbd74118bbe26987f54dcc77
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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