Isophthalic Acid → HCID 53657616, compound

HRID 1636136Notes

Reaction equation

HRID 1636136 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([C:26]([OH:28])=O)[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([OH:25])=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:23](=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:26]([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:28])[CH:18]=1)=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 8496Isophthalic AcidHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 53657616HCID 53657616, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using General Procedure A with 5.8 g (24.0 mmol) D-Proline benzyl ester hydrochloride and 2.0 g (12.0 mmol) benzene-1,3-dioic acid afforded, after flash chromatography (EtOAc), 4.68 g (72%) of the title compound as a yellow oil. MS m/e (%): 558 (M+NH4+, 100), 541 (M+H+, 90).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-6dfd68b96de1402286f52230ec786df8
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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