p-Phenylenediacetic acid → (s)-1-[[4-[2-[(s)-2-Benzyloxycarbonyl-pyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-pyrrolidine-2-carboxylic acid benzyl ester

HRID 1583181Notes

Reaction equation

HRID 1583181 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][C:20]([CH2:23][C:24]([OH:26])=O)=[CH:19][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:28](=[O:30])[CH2:27][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][C:24]([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:26])=[CH:21][CH:22]=1)=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 81760p-Phenylenediacetic acidHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 53878409(s)-1-[[4-[2-[(s)-2-Benzyloxycarbonyl-pyrrolidin-1-yl]-2-oxo-ethyl]-phenyl]-acetyl]-pyrrolidine-2-carboxylic acid benzyl esterYield 91.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using General Procedure A with 1.0 g (4.1 mmol) L-Proline benzyl ester hydrochloride and 400 mg (2.1 mmol) 1,4-phenylenediacetic acid afforded, after flash chromatography (EtOAc), 1.07 g (91%) of the title compound as a colorless oil.

Workup

  1. customafforded

Sources & evidence

ORD record
ord-202bf8be12074530b19e08f3ad9f9912
Source dataset
uspto-grants-2004_05
Patent number
US06740760B2

Reaction notes

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