Dimethylformamide → HCID 178472208, compound

HRID 965153Notes

Reaction equation

HRID 965153 reaction equation
[H-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[SH:13].[CH2:14]([O:16][C:17](=[O:35])[C:18]([CH3:34])([O:31][CH2:32][CH3:33])[CH:19]([PH:23](COS(C)(=O)=O)=[O:24])[CH:20]([CH3:22])[CH3:21])[CH3:15].[CH3:36]N(C=O)C>>[CH2:14]([O:16][C:17](=[O:35])[C:18]([CH3:34])([O:31][CH2:32][CH3:33])[C:19]([CH2:36][S:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:3]=1)([PH2:23]=[O:24])[CH:20]([CH3:21])[CH3:22])[CH3:15]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 178418736HCID 178418736, compoundHCID 178472205HCID 178472205, compound

Product 1

HCID 178472208HCID 178472208, compoundYield 80%

Procedure

Sodium hydride (1.52 g, (60%)) and 6 g of 2-quinoline thiol were stirred together at 0° C. in 50 mL DMF. After the initial H2 evolution had subsided, the mixture was stirred at room temperature for 21/2 hours. The mixture was then cooled to 0° C. and 2-(ethoxy) (methanesulfonyloxymethyl)phosphinoyl-methyl-4-methylpentanoic acid ethyl ester (12.8 g) in 10 mL DMF was added via cannula and the resulting mixture was then stirred for 18 hours, slowly warming to room temperature. The DMP was removed by evaporation, the residue dissolved in 50 mL ethyl acetate and washed with 50 mL H2O (2×), brine (50 mL), dried with MgSO4 and evaporated to a yellow semi-solid. Purification by flash chromatography using 10% ethyl acetate/hexane to 80% ethyl acetate/hexane for the elution yielded 10 g of 2-(ethoxy) (quinolin-2-ylthiomethyl)-phosphinoyl-methyl-4-methylpentanoic acid ethyl ester (Rf 0.35 80% ethyl acetate/hexane), MS: 424 (MH+).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. stirringthe resulting mixture was then stirred for 18 hours
  3. temperatureslowly warming to room temperature
  4. customThe DMP was removed by evaporation
  5. dissolutionthe residue dissolved in 50 mL ethyl acetate
  6. washwashed with 50 mL H2O (2×), brine (50 mL)
  7. dry with materialdried with MgSO4
  8. customevaporated to a yellow semi-solid
  9. customPurification by flash chromatography
  10. washfor the elution

Sources & evidence

ORD record
ord-4855a34892a641b9a666c62a75a6c406
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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