4-Nitrophenol → 4-Nitrophenyl (2S)-3-benzoylthio-2-methylpropionate

HRID 1003648Notes

Reaction equation

HRID 1003648 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:26]([S:34][CH2:35][C@@H:36]([CH3:40])[C:37](O)=[O:38])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:26]([S:34][CH2:35][C@@H:36]([CH3:40])[C:37]([O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:38])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 12763916(S)-3-(benzoylthio)-2-methylpropionic acid

Product 1

HCID 154536594-Nitrophenyl (2S)-3-benzoylthio-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenol (10.2 g) and dicyclohexylcarbodiimide (15.2 g) are added successively to a solution of (2S)-3-(benzoylthio)-2-methylpropionic acid (15 g) in methylene chloride (100 ml) under ice-cooling. The mixture is stirred under ice-cooling for 30 minutes and at room temperature for 4.5 hours. The resulting precipitate is filtered out, and the filtrate is concentrated under reduced pressure. The obtained oily residue is purified by silica gel column chromatography to give 26.01 g (quantitatively) of the titled compound.

Workup

  1. temperaturecooling
  2. filtrationThe resulting precipitate is filtered out
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe obtained oily residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9ad6560d7b844916ac13857c8141a9e1
Source dataset
uspto-grants-2000_04
Patent number
US06046235

Reaction notes

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