Triethylamine → HCID 14794471, compound

HRID 732862Notes

Reaction equation

HRID 732862 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([OH:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C(N(CC)CC)C.[O:23](S(C)(=O)=O)[S:24]([CH3:27])(=O)=[O:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([O:14][S:24]([CH3:27])(=[O:25])=[O:23])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 4092621Ethyl 2-hydroxy-4-phenylbutyrate, (+-)-

Product 1

HCID 14794471HCID 14794471, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl-2-hydroxy-4-phenylbutyrate (2.08 g, 10 mmol) in CH2Cl2 (20 mL) was added triethylamine (2.1 mL, 15 mmol) and Ms2O (1.92 g, 11 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 15 min. DMAP (50 mg) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 4 hours. The reaction was quenched with saturated NaHCO3. The resulting mixture was extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried (Na2SO4), filtered and CH2Cl2 was removed under reduced pressure. The residue was purified by flash chromatography (CH2Cl2), giving 2.7 g (94%) of the title compound. 13C NMR (CDCl3): 6169.3, 140.0, 128.9, 128.8, 126.7, 62.3, 52.8, 39.5, 33.9, 31.2, 14.3.

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. customThe reaction was quenched with saturated NaHCO3
  4. extractionThe resulting mixture was extracted with CH2Cl2 (3×50 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. customCH2Cl2 was removed under reduced pressure
  8. customThe residue was purified by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-d00da8a98c084df885e19bcf520d1f39
Source dataset
uspto-grants-2009_09
Patent number
US07589067B2

Reaction notes

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