Potassium Acetate → HCID 58294803, compound

HRID 422168Notes

Reaction equation

HRID 422168 reaction equation
FC(F)(F)S(OC1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]2[C:8]=1[C@@:9]1([CH3:30])[C@H:18]([CH2:19][S:20]2)[C@:17]2([CH3:27])[C@H:12]([C:13]([CH3:29])([CH3:28])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]1)(=O)=O.[CH3:33][C:34]([O-:36])=[O:35].[K+]>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C(Cl)Cl>[CH3:26][O:25][C:23]1[CH:22]=[C:21]2[C:8]([C@@:9]3([CH3:30])[C@H:18]([CH2:19][S:20]2)[C@:17]2([CH3:27])[C@H:12]([C:13]([CH3:29])([CH3:28])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]3)=[C:33]([C:34]([OH:36])=[O:35])[CH:24]=1

Participants

6

Reactant 2

HCID 517044Potassium AcetateHCID 53241983HCID 53241983, compound

Product 1

HCID 58294803HCID 58294803, compoundYield 34.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178478483HCID 178478483, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl trifluoromethanesulfonate (32) (1.5 g, 3.0 mmol), KOAc (1.1 g, 12 mmol), Pd(OAc)2 (0.3 g, 2 mmol), dppf:CH2Cl2 1:1 (0.97 g, 1.3 mmol) was prepared in DMSO (15 mL) and purged with N2. The reaction mixture was subjected to carbon monoxide via a balloon. The mixture was stirred at 60° C. for 18 h. The reaction was cooled to room temperature and quenched with water, acidified with 1 M HCl and extracted with EtOAc. The organic layer was concentrated to dryness. The crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 1:1) to yield (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carboxylic acid (74) (0.40 g, 34%) as a brown solid.

Workup

  1. custompurged with N2
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated to dryness
  6. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 1:1)

Sources & evidence

ORD record
ord-55a8882ac3d34ab5a65f1a463815a4ed
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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