1-((Tert-butoxy)carbonyl)-3,3-dimethylpyrrolidine-2-carboxylic acid → 1-(tert-butoxycarbonyl)-3,3-dimethylprolyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide

HRID 1058323Notes

Reaction equation

HRID 1058323 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[CH:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([O:22][C:23]([NH:25][CH2:26][C:27]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:28]=1[CH2:29][NH:30][C:31](=[O:37])[C@@H:32]1[CH2:36][CH2:35][CH2:34][NH:33]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(Cl)CCl>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C@H:9]1[C:10]([N:33]1[CH2:34][CH2:35][CH2:36][C@H:32]1[C:31]([NH:30][CH2:29][C:28]1[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:27]=1[CH2:26][NH:25][C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])=[O:37])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 40595971-((Tert-butoxy)carbonyl)-3,3-dimethylpyrrolidine-2-carboxylic acidHCID 11428605L-prolin-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)amide

Product 1

HCID 699375411-(tert-butoxycarbonyl)-3,3-dimethylprolyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-(tert-Butoxycarbonyl)-3,3-dimethylprolyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide was prepared as a mixture of diastereomers from 1-(tert-butoxycarbonyl)-3,3-dimethyl-D,L-proline (73 mg, 0.30 mmol) and L-prolin-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)amide (111 mg, 0.30 mmol) essentially according to the EDC coupling procedure described in Step 3 of Example 46. The diastereomeric products were separated by reverse phase HPLC as described in Step 3 of Example 46. Diastereomer A: LCMS RT=2.44 min. LCMS (M+H)=593.4. Diastereomer B: LCMS RT=2.58 min. LCMS (M+H)=593.5.

Workup

  1. customThe diastereomeric products were separated by reverse phase HPLC

Sources & evidence

ORD record
ord-db440c9ff5b24763a6a65d67be837703
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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