Benzoic Acid → (2R)-2-Benzoyloxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate

HRID 1600913Notes

Reaction equation

HRID 1600913 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]1([CH3:34])[CH:18]=[CH:17][C:16]([S:19]([O:22][CH2:23][C@@H:24]([OH:33])[CH2:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:54](O)(=[O:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>O1CCCC1>[C:13]1([CH3:34])[CH:18]=[CH:17][C:16]([S:19]([O:22][CH2:23][C@H:24]([O:33][C:54](=[O:61])[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57064601(2S)-2-hydroxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate

Product 1

HCID 53780759(2R)-2-Benzoyloxy-4-(3-pyridyl)-1-butyl para-toluenesulfonateYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.61 ml) was added to a solution of (2S)-2-hydroxy-4-(3-pyridyl)-1-butyl para-toluenesulfonate (1.4 g), triphenylphosphine (1.31 g) and benzoic acid (0.61 g) in tetrahydrofuran (30 ml) at 0° C. and the resulting solution stirred for 1 hour. The mixture was concentrated under reduced pressure and the residue obtained purified by column chromatography over silica eluting with diethyl ether to give the sub-title compound as a white solid (1.2 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. custompurified by column chromatography over silica eluting with diethyl ether

Sources & evidence

ORD record
ord-85da5f34290048f1869a59e7925a0a7e
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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