m-Phenylenediacetic acid → HCID 54405893, compound

HRID 1385751Notes

Reaction equation

HRID 1385751 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.[C:17]1([CH2:27][C:28]([OH:30])=O)[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]([OH:26])=O)[CH:18]=1>CCOC(C)=O>[CH2:2]([O:9][C:10]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:24](=[O:26])[CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH2:27][C:28]([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:30])[CH:18]=1)=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 29788m-Phenylenediacetic acidHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 54405893HCID 54405893, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using General Procedure A with 2.0 g (8.2 mmol) D-Proline benzyl ester hydrochloride and 800 mg (4.1 mmol) 1,3-phenylenediacetic acid afforded, after flash chromatography (EtOAc), 1.93 g (84%) of the title compound as a colorless oil. MS m/e (%): 586 (M+NH4+, 100), 569 (M+H+, 60).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-19b38333243d43fa9a11b0bcb381466f
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

Loading…