(1R,2R)-(-)-1,2-Cyclohexanedicarboxylic acid → [(1S,2S)-2-[(R)-2-carboxy-pyrrolidine-1-carbonyl]-cyclohexanecarbonyl]-pyrrolidine-2-carboxylic acid

HRID 1583172Notes

Reaction equation

HRID 1583172 reaction equation
Cl.C([O:9][C:10](=[O:16])[C@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)C1C=CC=CC=1.[C@@H:17]1([C:26]([OH:28])=O)[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([OH:25])=O>CCOC(C)=O>[C:10]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:23]([C@H:18]1[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]1[C:26]([N:12]1[CH2:13][CH2:14][CH2:15][CH:11]1[C:10]([OH:9])=[O:16])=[O:28])=[O:25])([OH:16])=[O:9]

Participants

4

Reactant 2

HCID 720895(1R,2R)-(-)-1,2-Cyclohexanedicarboxylic acidHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 23557523[(1S,2S)-2-[(R)-2-carboxy-pyrrolidine-1-carbonyl]-cyclohexanecarbonyl]-pyrrolidine-2-carboxylic acidYield 90.5%

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 700 mg (4.1 mmol) trans-cyclohexane-1,2-dicarboxylic acid afforded, after flash chromatography (EtOAc), 1.36 g (62%) of the title compound as a colorless oil. MS m/e (%): 547 (M+H+, 100).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-93bba73e18db4c618f0c673c3d5fd632
Source dataset
uspto-grants-2004_05
Patent number
US06740760B2

Reaction notes

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