Potassium Carbonate → HCID 178525820, compound

HRID 1192732Notes

Reaction equation

HRID 1192732 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.Cl.C[O:16][C:17](=[O:26])[C@@H:18]([NH2:25])[CH2:19][S:20][CH2:21][CH:22]1[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+:31].[K+]>C(O)(C)C>[CH:22]1([CH2:21][S:20][CH2:19][C@H:18](/[N:25]=[C:3](/[C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)\[C:2]([F:13])([F:12])[F:1])[C:17]([O-:26])=[O:16])[CH2:24][CH2:23]1.[K+:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 70945878HCID 70945878, compound

Product 1

HCID 178525820HCID 178525820, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of 2,2,2,4′-tetrafluoroacetophenone (48 g; 250 mmol) and (R)-methyl2-amino-3-((cyclopropylmethyl)thio)propanoate hydrochloride (56.4 g; 250 mmol) in isopropanol (IPA; 1100 mL) was added potassium carbonate (69.1 g; 500 mmol; 200 mole %) and the mixture heated at 50-60° C. under a nitrogen atmosphere. After 46 h, the reaction mixture was filtered hot through a pad of celite that was prewashed with hot IPA. The filter was washed with hot IPA (2×) and the combined filtrate and washes were distilled to about 90% of the original volume. Acetonitrile (ACN) was added and the solvent was distilled. This process was repeated two more times with ACN and the product was evaporated to dryness. Potassium (R,Z)-3-((cyclopropylmethyl)thio)-2-((2,2,2-trifluoro-1-(4-fluorophenyl)ethylidene)-amino)propanoate (87 g; 90%) was obtained after drying under high vacuum (1 mm Hg) for 2 hours. This material was used in the next reaction without further purification.

Workup

  1. filtrationthe reaction mixture was filtered hot through a pad of celite that
  2. washThe filter was washed with hot IPA (2×)
  3. distillationthe combined filtrate and washes were distilled to about 90% of the original volume
  4. additionAcetonitrile (ACN) was added
  5. distillationthe solvent was distilled
  6. customthe product was evaporated to dryness

Sources & evidence

ORD record
ord-2b389a52d83f4307949fc7b0e0f17a34
Source dataset
uspto-grants-2014_03
Patent number
US08680152B2

Reaction notes

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