2,4-Dimethylglutaric acid → HCID 53886375, compound

HRID 1636129Notes

Reaction equation

HRID 1636129 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.[CH3:17][CH:18]([CH2:22][CH:23]([CH3:27])[C:24]([OH:26])=O)[C:19]([OH:21])=O>CCOC(C)=O>[CH2:2]([O:9][C:10]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:19](=[O:21])[CH:18]([CH3:17])[CH2:22][CH:23]([CH3:27])[C:24]([N:12]1[CH2:13][CH2:14][CH2:15][C@@H:11]1[CH2:10][O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:26])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 978702,4-Dimethylglutaric acidHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 53886375HCID 53886375, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using General Procedure A with 6.05 g (25 mmol) D-Proline benzyl ester hydrochloride and 2.0 g (12.5 mmol) 2,4-dimethylglutaric acid afforded, after flash chromatography (EtOAc), 4.3 g (64%) of the title compound as a light yellow oil. MS m/e (%): 535 (M+H+, 100).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-c969a8c7501342a58e0b2b52bd55274a
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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