Potassium Carbonate → HCID 25152882, compound

HRID 1891424Notes

Reaction equation

HRID 1891424 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[C:18]([OH:24])=[CH:19][CH:20]=[C:21]([F:23])[CH:22]=2)[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C:11]1([CH3:16])[CH3:15])=[O:9].CC1C=CC(S(O[C@H:36]([CH3:41])[C:37]([O:39][CH3:40])=[O:38])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24][C@@H:36]([CH3:41])[C:37]([O:39][CH3:40])=[O:38])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C:11]1([CH3:16])[CH3:15])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12884153(R)-2-Tosyloxypropionic acid methyl esterHCID 25152881HCID 25152881, compound

Product 1

HCID 25152882HCID 25152882, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

The intermediate from step d) (2.83 g) was dissolved in MeCN (30 mL). The product from step e) (2.11 g) and potassium carbonate (2.25 g) were added and the mixture was heated to 65° C. for 16 h. The mixture was cooled to rt and extracted with diethyl ether (×2), dried (MgSO4) and concentrated under reduced pressure to give an oil. The oil was purified by flash column chromatography on silica using isohexane 3:1 ethyl acetate as eluent to give the sub titled product as a colourless oil (2.29 g).

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionextracted with diethyl ether (×2)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil
  6. customThe oil was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-b3e2c92ef3b14d3a94641a63e83d8e30
Source dataset
uspto-grants-2013_08
Patent number
US08507544B2

Reaction notes

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