Potassium Carbonate → HCID 19025070, compound

HRID 1033947Notes

Reaction equation

HRID 1033947 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[OH:7][CH2:8][CH:9]([O:12][C:13]1[CH:18]=CC=C[CH:14]=1)[CH:10]=[CH2:11]>CO>[OH:7][CH2:8][CH:9]([O:12][C:13]([CH3:14])([CH3:18])[CH3:1])[CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 13776066HCID 13776066, compound2×

Product 1

HCID 19025070HCID 19025070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

This half-ester R-3k (104 mg; 0.4 mmol) was dissolved in methanol (5 mL) and treated with potassium carbonate (110 mg; 0.8 mmol; 2 equiv.) and stirred overnight to completely consume 3k (tlc analysis). The reaction mixture was diluted with water (25 mL) and ether (25 mL) and the layers were separated. The aqueous layer was extracted with ether (2×15 mL). The combined organic solution was dried (MgSO4) and concentrated to afford 62 mg (94%) of R-1k. All achiral properties of 1k are as reported above. [α]D20 -14.2° (C. 1.01, CH3OH). The absolute configuration of 1k was inferred to be R-(-) by analogy with the absolute configuration results of the enzymatic reaction of 1j. 1H nmr analysis of the MTPA ester using an analogous procedure to that of Dale et al., J. Org. Chem., 1969, 34, 2543, indicated 54% ee for R-1k.

Workup

  1. customto completely consume 3k (tlc analysis)
  2. additionThe reaction mixture was diluted with water (25 mL) and ether (25 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ether (2×15 mL)
  5. dry with materialThe combined organic solution was dried (MgSO4)
  6. concentrationconcentrated
  7. customto afford 62 mg (94%) of R-1k

Sources & evidence

ORD record
ord-9e0afd48294245a199f4d2633b74a02a
Source dataset
uspto-grants-1994_05
Patent number
US05312950

Reaction notes

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