2,5-Dihydroxy-p-benzenediacetic acid → HCID 54109210, compound

HRID 1385750Notes

Reaction equation

HRID 1385750 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:17][C:18]1[CH:23]=[C:22]([CH2:24][C:25]([OH:27])=O)[C:21]([OH:28])=[CH:20][C:19]=1[CH2:29][C:30]([OH:32])=O>CCOC(C)=O.CCCCCC>[CH2:2]([O:9][C:10]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:30](=[O:32])[CH2:29][C:19]1[CH:20]=[C:21]([OH:28])[C:22]([CH2:24][C:25]([N:12]2[CH2:13][CH2:14][CH2:15][C@@H:11]2[C:10]([O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:16])=[O:27])=[CH:23][C:18]=1[OH:17])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 796282,5-Dihydroxy-p-benzenediacetic acidHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 54109210HCID 54109210, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using General Procedure A with 10.7 g (44.2 mmol) D-Proline benzyl ester hydrochloride and 5.0 g (22.1 mmol) 2,5-dihydroxy-1,4-phenylenediacetic acid afforded, after flash chromatography (gradient: 70-100% EtOAc/hexane), 3.17 g (24%) of the title compound as a colorless foam. MS m/e (%): 601 (M+H+, 100).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-ba0885d924e84c7d89eab81aef8cbe2f
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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