Potassium Carbonate → HCID 54200145, compound

HRID 1733340Notes

Reaction equation

HRID 1733340 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Br[CH:10]([C:14]([F:17])([F:16])[F:15])[C:11](Cl)=[O:12].[S:18]1C=C[CH:20]=[C:19]1CC(O)=O.C(=O)([O-])[O-].[K+].[K+].[OH-:33].[Na+]>O>[C:19]([S:18][CH:10]([C:14]([F:17])([F:16])[F:15])[C:11]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:12])(=[O:33])[CH3:20]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 159702-Thiopheneacetic acidHCID 145742L-ProlineHCID 540458592-Bromo-3,3,3-trifluoropropanoyl chloride

Product 1

HCID 54200145HCID 54200145, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of L-proline (5.75 g.) in 1 N sodium hydroxide (50 ml), chilled in an ice-water bath, 2-bromo-3,3,3-trifluoropropanoic acid chloride (12 g.) is added and the mixture is vigorously stirred at room temperature for three hours. A solution of thiolacetic acid (4 ml.) and potassium carbonate (4.8 g.) in water (50 ml.) is added and the mixture is stirred at room temperature for sixteen hours. After extraction with ethyl acetate, the aqueous layer is acidified with concentrated hydrochloric acid and extracted again with ethyl acetate. This last organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo. The residue is chromatographed on a silica gel column with a mixture of benzeneacetic acid (7:2) to yield 1-(2-acetylthio-3,3,3-trifluoropropanoyl)-L-proline.

Workup

  1. stirringthe mixture is stirred at room temperature for sixteen hours
  2. extractionAfter extraction with ethyl acetate
  3. extractionextracted again with ethyl acetate
  4. dry with materialThis last organic phase is dried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue is chromatographed on a silica gel column with a mixture of benzeneacetic acid (7:2)

Sources & evidence

ORD record
ord-7a3de8e3b24c4fb1972ec58f1d6f808f
Source dataset
uspto-grants-1980_12
Patent number
US04241076

Reaction notes

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