Methyl iodide → (2S,4R)-4-(Aminomethyl)-N-methyl-N-[(1R)-3-methyl-1-(6-ethyl-3-quinolylcarbamoyl)butyl]-2-pyrrolidinecarboxamide

HRID 2185498Notes

Reaction equation

HRID 2185498 reaction equation
C(O[C:6]([N:8]([CH3:17])[C@@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])(C)(C)C.C(OC(N[C@@H](C(O)=O)CC(C)C)=O)(C)(C)C.[H-].[Na+].CI.C(OC(NCC(N[C@H]1CN(C(OC(C)(C)C)=O)[C@H](C(O)=O)C1)=O)=O)(C)(C)C.C(OC([NH:72][CH2:73][C@@H:74]1[CH2:78][N:77](C(OC(C)(C)C)=O)[C@@H:76](C(O)=O)[CH2:75]1)=O)(C)(C)C.[NH2:89][C:90]1[CH:91]=[N:92][C:93]2[C:98]([CH:99]=1)=[CH:97][C:96]([CH2:100][CH3:101])=[CH:95][CH:94]=2.NC1C=NC2C(C=1)=CC=CC=2>>[NH2:72][CH2:73][C@@H:74]1[CH2:78][NH:77][C@H:76]([C:6]([N:8]([CH3:17])[C@@H:9]([C:14](=[O:16])[NH:89][C:90]2[CH:91]=[N:92][C:93]3[C:98]([CH:99]=2)=[CH:97][C:96]([CH2:100][CH3:101])=[CH:95][CH:94]=3)[CH2:10][CH:11]([CH3:12])[CH3:13])=[O:7])[CH2:75]1

Participants

9

Reactant 8

HCID 6328Methyl iodideHCID 113753-AminoquinolineHCID 24758Sodium hydrideHCID 637604tert-Butoxycarbonyl-D-leucineHCID 6992561Boc-N-methyl-D-leucineHCID 21341559trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-prolineHCID 224587516-Ethylquinolin-3-amineHCID 53725027trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-D-proline

Product 1

HCID 70175963(2S,4R)-4-(Aminomethyl)-N-methyl-N-[(1R)-3-methyl-1-(6-ethyl-3-quinolylcarbamoyl)butyl]-2-pyrrolidinecarboxamide

Procedure

This compound was prepared as for Compound M15, replacing N-tert-butoxycarbonyl-D-homophenylalanine with N-tert-butoxycarbonyl-N-methyl-D-leucine (made by treantment of N-tert-butoxycarbonyl-D-leucine with excess sodium hydride and methyl iodide in 1TF), trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-proline with trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-D-proline and coupling with 3-amino-6-ethylquinoline inst of 3-aminoquinoline.

Workup

  1. customThis compound was prepared as for Compound M15

Sources & evidence

ORD record
ord-1650b4ffa68945d7887911f37d9fb329
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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