3-Methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester → HCID 69656059, compound

HRID 857767Notes

Reaction equation

HRID 857767 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([N:33]2[CH:37]=[N:36][N:35]=[N:34]2)=[C:22]([CH:32]=1)[CH2:23][NH:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1>C(Cl)CCl>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]([CH3:16])[C@H:9]1[C:10]([N:27]1[CH2:28][CH2:29][CH2:30][C@H:26]1[C:25]([NH:24][CH2:23][C:22]1[CH:32]=[C:18]([Cl:17])[CH:19]=[CH:20][C:21]=1[N:33]1[CH:37]=[N:36][N:35]=[N:34]1)=[O:31])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 5818343-Methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl esterHCID 69655818N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

Product 1

HCID 69656059HCID 69656059, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared as a mixture of diastereomers from 1-(tert-butoxycarbonyl-3-methyl-dl-proline (16 mg, 0.07 mmol) and N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (Example 26, Step B, 21 mg, 0.07 mmol), essentially according to the EDC coupling procedure described in Example 39, Step D. The diastereomeric products were separated by reverse phase HPLC and were carried on directly to deprotection.

Workup

  1. customThe diastereomeric products were separated by reverse phase HPLC

Sources & evidence

ORD record
ord-ce5b54ae7f964ea1af3c30ceec69f09b
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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