Potassium Carbonate → HCID 59552179, compound

HRID 1876301Notes

Reaction equation

HRID 1876301 reaction equation
C([O:4][C@H:5](/[CH:7]=[CH:8]\[C:9]([NH:11][C@@H:12]1[CH2:17][C@H:16]([CH3:18])[C@H:15]([CH2:19]/[CH:20]=[C:21](\[CH3:24])/[CH:22]=[CH2:23])[O:14][C@@H:13]1[CH3:25])=[O:10])[CH3:6])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.[NH4+].[Cl-]>[CH3:25][C@@H:13]1[C@H:12]([NH:11][C:9](=[O:10])/[CH:8]=[CH:7]\[C@@H:5]([OH:4])[CH3:6])[CH2:17][C@H:16]([CH3:18])[C@H:15]([CH2:19]/[CH:20]=[C:21](\[CH3:24])/[CH:22]=[CH2:23])[O:14]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 11660299HCID 11660299, compound

Product 1

HCID 59552179HCID 59552179, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of (S,Z)-5-((2R,3R,5S,6S)-2,5-dimethyl-6-((E)-3-methylpenta-2,4-dienyl)-tetrahydro-2H-pyran-3-ylamino)-5-oxopent-3-en-2-yl acetate (26.5 mg, 0.0758 mmol) in MeOH (380 μL) was added K2CO3 (26.3 mg, 0.190 mmol) at 0° C. under an open atmosphere. After 2 h at the same temperature the reaction was diluted with saturated aqueous NH4Cl (60 μL) and stirred for 5 min. The resulting reaction mixture was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (20→50% EtOAc in hexanes) on silica gel (3 mL) to give (S,Z)—N-((2R,3R,5S,6S)-2,5-dimethyl-6-((E)-3-methylpenta-2,4-dienyl)-tetrahydro-2H-pyran-3-yl)-4-hydroxypent-2-enamide (19.2 mg, 82%) as a colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. dry with materialwas dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by flash chromatography (20→50% EtOAc in hexanes) on silica gel (3 mL)

Sources & evidence

ORD record
ord-c5ee048a25764886ac430b7fc20c4db4
Source dataset
uspto-grants-2012_11
Patent number
US08309599B2

Reaction notes

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