Water → HCID 53830722, compound

HRID 2288011Notes

Reaction equation

HRID 2288011 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C@@H:5]([CH:17]([CH3:19])[CH3:18])[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13](F)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:2].[C:21]1([SH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[C@@H:5]([CH:17]([CH3:19])[CH3:18])[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([S:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 53694813HCID 53694813, compound

Product 1

HCID 53830722HCID 53830722, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 7.76 g (25.6 mmol) of N-[(4-fluorophenyl)sulfonyl]-D-valine ethyl ester from Example 7a in 50 mL of anhydrous dimethylformamide was added 7.8 mL (77 mmol) of thiophenol. After purging with nitrogen for 5 minutes, 10.6 g (77 mmol) of powdered potassium carbonate was added and the reaction heated to 70° C. for 21 hours. The solution was cooled, water and ethyl acetate added and separated. The ethyl acetate layer was washed with saturated sodium bicarbonate, three times with brine, dried with sodium sulfate, filtered and concentrated to afford crude product. This was chromatographed on silica gel using 20% ethyl acetate/hexane to yield 4.2 g of N-[[4-(phenylthio)phenyl]sulfonyl]-D-valine ethyl ester, m/e=400 (M+Li).

Workup

  1. customAfter purging with nitrogen for 5 minutes
  2. temperatureThe solution was cooled
  3. customseparated
  4. washThe ethyl acetate layer was washed with saturated sodium bicarbonate, three times with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford crude product
  9. customThis was chromatographed on silica gel using 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-211a3f7223ed4891babf024ca679419e
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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