benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride → HCID 53839178, compound

HRID 1385759Notes

Reaction equation

HRID 1385759 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]([CH2:20][C:21]1[N:26]=[C:25]([CH2:27][C:28]([OH:30])=O)[CH:24]=[CH:23][CH:22]=1)([OH:19])=O>CO.CCOC(C)=O>[CH2:2]([O:9][C:10]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:17](=[O:19])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([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])[N:26]=1)=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochlorideHCID 23422430HCID 23422430, compound

Product 1

HCID 53839178HCID 53839178, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Using General Procedure A with 9.7 g (40 mmol) D-Proline benzyl ester hydrochloride and 3.9 g (20 mmol) (6-carboxymethyl-pyridin-2-yl)-acetic acid afforded, after flash chromatography (gradient: 0-10% MeOH/EtOAc), 890 mg (8%) of the title compound as a yellow oil. MS m/e (%): 570 (M+H+, 100).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-cc849392ae04442584dbc6a9f7f387e7
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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