Oxalyl chloride → 4-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyryl chloride

HRID 1493442Notes

Reaction equation

HRID 1493442 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH2:7]([O:9][C:10]([C@H:12]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:13][C@@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15](O)=[O:16])=[O:11])[CH3:8]>C(Cl)Cl>[CH2:7]([O:9][C:10]([C@H:12]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:13][C@@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([Cl:4])=[O:16])=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 145577314-ethoxycarbonyl(S,S)-2,4-dibenzylbutyric acid

Product 1

HCID 149971304-ethoxycarbonyl-(S,S)-2,4-dibenzylbutyryl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-ethoxycaronyl-(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. customevaporated

Sources & evidence

ORD record
ord-7a3ce01095a14097a9b2d71f6690a91a
Source dataset
uspto-grants-1991_06
Patent number
US05021430

Reaction notes

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