tert-Butyl (2S)-2-[({4-[2-(benzyloxy)-2-oxoethyl]-6-chloro-5-methyl-3-oxo-3,4-dihydro-2-pyrazinyl}amino)methyl]-1-pyrrolidinecarboxylate → 2-[3-({[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]methyl}amino)-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic Acid

HRID 2228758Notes

Reaction equation

HRID 2228758 reaction equation
C([O:8][C:9](=[O:34])[CH2:10][N:11]1[C:16]([CH3:17])=[C:15]([Cl:18])[N:14]=[C:13]([NH:19][CH2:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:12]1=[O:33])C1C=CC=CC=1>[OH-].[Pd+2].[OH-]>[C:29]([O:28][C:26]([N:22]1[CH2:23][CH2:24][CH2:25][C@H:21]1[CH2:20][NH:19][C:13]1[C:12](=[O:33])[N:11]([CH2:10][C:9]([OH:34])=[O:8])[C:16]([CH3:17])=[C:15]([Cl:18])[N:14]=1)=[O:27])([CH3:30])([CH3:31])[CH3:32]

Participants

3

Reactant 1

HCID 59900522tert-Butyl (2S)-2-[({4-[2-(benzyloxy)-2-oxoethyl]-6-chloro-5-methyl-3-oxo-3,4-dihydro-2-pyrazinyl}amino)methyl]-1-pyrrolidinecarboxylate

Product 1

HCID 699638462-[3-({[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]methyl}amino)-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic Acid

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

The title compound was prepared by a similar method to preparation 44 from tert-butyl (2S)-2-[({4-[2-(benzyloxy)-2-oxoethyl]-6-chloro-5-methyl-3-oxo-3,4-dihydro-2-pyrazinyl}amino)methyl]-1-pyrrolidinecarboxylate [see preparation 64] and palladium hydroxide. The title compound was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (90:10:0.5) changing to (80:20:3), to afford the product as a colourless oil, (44%).

Workup

  1. customThe title compound was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-992ef52a9de549f6884a1de8e8ac5604
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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