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Cyclopentylamine → (R)-tert-butyl 1-(cyclopentylamino)-3-hydroxy-3-methyl-1-oxobutan-2-ylcarbamate

HRID 1968226
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HRID 1968226 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=N[C:27]2[CH:28]=[CH:29][CH:30]=[N:31][C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CCCC1.CCN(CC)CC>C(Cl)Cl>[CH:26]1([NH:31][C:10](=[O:12])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:13]([OH:16])([CH3:15])[CH3:14])[CH2:27][CH2:28][CH2:29][CH2:30]1
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HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11299247N-(tert-Butoxycarbonyl)-3-hydroxy-D-valine

생성물 1

HCID 67224582(R)-tert-butyl 1-(cyclopentylamino)-3-hydroxy-3-methyl-1-oxobutan-2-ylcarbamate수율 93.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of (R)-2-(tert-butoxycarbonylamino)-3-hydroxy-3-methylbutanoic acid (0.5 g, 2.144 mmol), HATU (0.978 g, 2.57 mmol) and cyclopentanamine (0.423 mL, 4.29 mmol) in DCM (10 mL) was added Et3N (0.598 mL, 4.29 mmol). The reaction mixture was stirred at room temperature for 5 h and then washed with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, concentrated, and purified by silica column chromatography (MeOH/DCM, 0-10%) to afford the title compound (0.6 g, 93%).

후처리

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. custompurified by silica column chromatography (MeOH/DCM, 0-10%)

출처 및 근거

ORD 기록
ord-49818e5bc6df4647b489e3bf845653c5
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08420816B2

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