Methanol → HCID 11155476, compound

HRID 2288027Notes

Reaction equation

HRID 2288027 reaction equation
CO.Cl.[CH:4]1([C:7]([CH:9]([N:17]2[CH2:22][CH2:21][CH:20]([SH:23])/[C:19](=[CH:24]/[C:25]([OH:27])=[O:26])/[CH2:18]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[O:8])[CH2:6][CH2:5]1.CSSC.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>C(#N)C.O.C(#N)C>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[CH:4]1([C:7]([CH:9]([N:17]2[CH2:22][CH2:21][CH:20]([SH:23])/[C:19](=[CH:24]\[C:25]([OH:27])=[O:26])/[CH2:18]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[O:8])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 12232Dimethyl DisulfideHCID 23000820HCID 23000820, compound

Product 1

HCID 11155476HCID 11155476, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

In 60 ml of a (1:1) mixed solvent of methanol and acetonitrile, 0.50 g (1.3 mmol) of (E)-1-(α-cylopropylcarbonyl-2-fluorobenzyl)-3-carboxymethylidene-4-mercaptopiperidine hydrochloride and 0.05 ml of dimethyl disulfide were dissolved, followed by exposure to light for 90 minutes under cooling by using a low-pressure mercury lamp of 32 W. After the completion of the reaction, the reaction mixture was concentrated by evaporation under reduced pressure. The residue was subjected to high-performance liquid chromatography (column: TSK-GEL ODS-80TS, mobile phase; acetonitrile/water=3/7 (containing 0.016% of trifluoroacetic acid), temperature: room temperature), whereby two diastereomers of the title compound, that is, 14.0 mg (Isomer A) and 13.5 mg (Isomer B) were obtained, each as white powder (amorphous). The retention times of Isomer A and Isomer B in high-performance liquid chromatography (column: Inertsil ODS-2, mobile phase: acetonitrile/water=20/80 (containing 0.02% of trifluoroacetic acid), temperature: 27° C., flow rate: 1.5 ml/min) were 16.5 minutes and 18.5 minutes, respectively.

Workup

  1. dissolutionwere dissolved
  2. temperatureunder cooling
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
  5. additionThe residue was subjected to high-performance liquid chromatography (column: TSK-GEL ODS-80TS, mobile phase; acetonitrile/water=3/7 (containing 0.016% of trifluoroacetic acid), temperature: room temperature), whereby two diastereomers of the title compound
  6. custom14.0 mg (Isomer A) and 13.5 mg (Isomer B) were obtained
  7. waitwere 16.5 minutes and 18.5 minutes

Sources & evidence

ORD record
ord-f18ba9530a43446da3b8046046b17da5
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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