Benzyl {6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}(4-{[N-({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)-N-methyl-beta-alanyl](methyl)amino}phenyl)carbamate → 1-{2-[{6-[(4-{[N-({[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)-N-methyl-beta-alanyl](methyl)amino}phenyl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate

HRID 446613노트

반응식

HRID 446613 반응식
[C:1]1([C:101]2[CH:106]=[CH:105][CH:104]=[CH:103][CH:102]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([CH3:100])[C:20](=[O:99])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([C:37]2[CH:42]=[CH:41][C:40]([N:43]([C:45](=[O:98])[CH2:46][CH2:47][N:48]([C:50](=[O:97])[CH2:51][O:52][C@@H:53]3[C:61]4([CH2:66][CH2:65][N:64]([CH2:67][CH2:68][C@:69]5([C:90]6[CH:95]=[CH:94][C:93]([F:96])=[CH:92][CH:91]=6)[O:73][CH2:72][N:71]([C:74](=[O:89])[C:75]6[CH:80]=[C:79]([C:81]([F:84])([F:83])[F:82])[CH:78]=[C:77]([C:85]([F:88])([F:87])[F:86])[CH:76]=6)[CH2:70]5)[CH2:63][CH2:62]4)[C:60]4[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=4)[CH2:54]3)[CH3:49])[CH3:44])=[CH:39][CH:38]=2)C(=O)OCC2C=CC=CC=2)[CH2:13][CH2:12]1)=[O:9]>C(O)C.C(OCC)(=O)C.[C].[Pd]>[C:1]1([C:101]2[CH:102]=[CH:103][CH:104]=[CH:105][CH:106]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:9])[O:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([C:20](=[O:99])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:37]2[CH:38]=[CH:39][C:40]([N:43]([C:45](=[O:98])[CH2:46][CH2:47][N:48]([C:50](=[O:97])[CH2:51][O:52][C@@H:53]3[C:61]4([CH2:66][CH2:65][N:64]([CH2:67][CH2:68][C@:69]5([C:90]6[CH:95]=[CH:94][C:93]([F:96])=[CH:92][CH:91]=6)[O:73][CH2:72][N:71]([C:74](=[O:89])[C:75]6[CH:80]=[C:79]([C:81]([F:82])([F:83])[F:84])[CH:78]=[C:77]([C:85]([F:87])([F:88])[F:86])[CH:76]=6)[CH2:70]5)[CH2:63][CH2:62]4)[C:60]4[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=4)[CH2:54]3)[CH3:49])[CH3:44])=[CH:41][CH:42]=2)[CH3:100])[CH2:13][CH2:12]1

참가 물질

5

반응물 1

HCID 86663479Benzyl {6-[(2-{4-[(biphenyl-2-ylcarbamoyl)oxy]piperidin-1-yl}ethyl)(methyl)amino]-6-oxohexyl}(4-{[N-({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)-N-methyl-beta-alanyl](methyl)amino}phenyl)carbamate

생성물 1

HCID 867619211-{2-[{6-[(4-{[N-({[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)-N-methyl-beta-alanyl](methyl)amino}phenyl)amino]hexanoyl}(methyl)amino]ethyl}piperidin-4-yl biphenyl-2-ylcarbamate수율 88.1%

시약·촉매·용매 3

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

The compound (180 mg, 0.12 mmol) obtained in Example 97f was dissolved in a mixed solvent of ethanol (3 mL) and ethyl acetate (3 mL), 10% palladium-carbon (36 mg, 20% by weight) was added, and the mixture was stirred at room temperature under a hydrogen atmosphere for 18 hours. After the reaction was completed, the reaction mixture was filtered through celite, the filtrate was washed with methanol, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol, 30:1, v/v) to give the title compound (141 mg; yield, 86%) as a white solid.

후처리

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through celite
  3. washthe filtrate was washed with methanol
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate

출처 및 근거

ORD 기록
ord-c17ffaa0fa5b44fb8252057e642e87f3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

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