phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(3-methyl-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate → (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(3-methyl-2-pyridinyl)-3-pyrazolidinecarboxamide

HRID 1396871노트

반응식

HRID 1396871 반응식
[CH:1]1([CH2:6][C@H:7]([CH2:35][N:36]([CH:45]=[O:46])[O:37]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2C(OCC2C=CC=CC=2)=O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:35][N:36]([CH:45]=[O:46])[OH:37])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][NH:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 1

HCID 86706345phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(3-methyl-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate

생성물 1

HCID 66546691(3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(3-methyl-2-pyridinyl)-3-pyrazolidinecarboxamide수율 37%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

To a solution of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(3-methyl-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate (179 mg, 0.285 mmol) in methanol (6 ml) was added 20% palladium hydroxide on carbon (72 mg, 0.285 mmol). The mixture was hydrogenated under balloon pressure for 1 h 15 min and then filtered. The mixture was purified by reverse-phase HPLC to yield (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(3-methyl-2-pyridinyl)-3-pyrazolidinecarboxamide (44 mg, 0.105 mmol, 37% yield). LC/MS: (M+H)+: 404.

후처리

  1. filtrationfiltered
  2. customThe mixture was purified by reverse-phase HPLC

출처 및 근거

ORD 기록
ord-e8b504d31fb84d4bae9d6bdfc3c20481
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901119B2

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