(S,S)-2,4-dibenzylglutaric anhydride → 4-ethoxycarbonyl(S,S)-2,4-dibenzylbutyric acid

HRID 374315Notes

Reaction equation

HRID 374315 reaction equation
[CH2:1]([C@@H:8]1[CH2:14][C@@H:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:22])[O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([OH:25])[CH3:24].C1(C)C=CC=CC=1>>[CH2:23]([O:25][C:12]([C@H:13]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:14][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([OH:11])=[O:10])=[O:22])[CH3:24]

Participants

3

Reactant 2

HCID 14557658(S,S)-2,4-dibenzylglutaric anhydrideHCID 21863594Toluene ethanol

Product 1

HCID 145577314-ethoxycarbonyl(S,S)-2,4-dibenzylbutyric acid

Procedure

The starting material is prepared as follows: 4.0 g of (S,S)-2,4-dibenzylglutaric anhydride is refluxed in 40 ml of ethanol:toluene (3:2) overnight. The reaction mixture is concentrated to yield 4-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyric acid as an oil. Oxalyl chloride (3.5 ml) is added to the solution of 4.5 g of 4-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyric acid in 10 ml of methylene chloride. The mixture is stirred at room temperature overnight and evaporated to yield 4-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyryl chloride, which is used as such without further purification.

Workup

  1. customThe starting material is prepared
  2. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-b7c14f1a699f44c79c5dd94cafcaa54b
Source dataset
uspto-grants-1992_11
Patent number
US05166212

Reaction notes

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