Trifluoroacetic acid → HCID 9822857, compound

HRID 1741687Notes

Reaction equation

HRID 1741687 reaction equation
[C:1]([O:5]C)(=[O:4])[CH2:2][SH:3].[CH3:7][C:8]([C:11]1[CH:16]=[C:15]([S:17][C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2O)[CH:14]=[C:13]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:12]=1[OH:29])([CH3:10])[CH3:9].FC(F)(F)C(O)=O.[OH-].[K+].O.[OH-].[Li+]>C(Cl)Cl.O.CO>[CH3:10][C:8]([C:11]1[CH:16]=[C:15]([S:17][C@@H:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]2[S:3][CH2:2][C:1]([OH:5])=[O:4])[CH:14]=[C:13]([C:25]([CH3:26])([CH3:27])[CH3:28])[C:12]=1[OH:29])([CH3:7])[CH3:9]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 16907Methyl ThioglycolateHCID 168937Lithium hydroxide, monohydrateHCID 15287673HCID 15287673, compound

Product 1

HCID 9822857HCID 9822857, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl thioglycolate (4.8 g, 0.0448 mole) was added to a solution of the compound of Example 15 (15.0 g, 0.0448 moles) in methylene chloride (20 ml). After stirring for 15 minutes, trifluoroacetic acid (18 ml) was added to the reaction mixture. The reaction mixture was stirred for 64 hours and then poured into methyl alcohol (100 ml) containing potassium hydroxide (13 g, 0.23 moles) and lithium hydroxide hydrate (9.7 g, 0.23 moles). Over the next 3 hours water was added to bring the final volume to 300 ml. The solution was washed twice with 150 ml of ethyl acetate. The aqueous layer was made acidic to pH 2 with concentrated hydrochloric acid. The reaction mixture was extracted twice with 200 ml of ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate, filtered and concentrated in vacuo to give the product as an oil. The product was purified by silica gel chromatography. The resulting oil was heated at 65° C. under vacuum to remove a trace amount of ethyl acetate. The structure assignment was supported by NMR, infrared spectroscopy, and elemental analysis.

Workup

  1. stirringThe reaction mixture was stirred for 64 hours
  2. washThe solution was washed twice with 150 ml of ethyl acetate
  3. extractionThe reaction mixture was extracted twice with 200 ml of ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e947bdc07b9a485eb7302dd776410d21
Source dataset
uspto-grants-1994_08
Patent number
US05334616

Reaction notes

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