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Hydrochloric Acid → 4-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylic acid

HRID 736409
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HRID 736409 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2([C:23]([O-:25])=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>CO.[OH-].[Na+]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2([C:23]([OH:25])=[O:24])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 866021164-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate

생성물 1

HCID 672319944-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylic acid수율 65.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 14798Sodium Hydroxide
용매

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온도
60 °C

실험 절차

To a solution of Methyl 4-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidin-1-yl) methyl]tetrahydro-2H-pyran-4-carboxylate (6.47 g, 17.5 mmol, Step 10) in MeOH (32 mL), 5 N NaOH aq (10 mL) was added at room temperature (exothermic). The resulting solution was stirred at 60° C. for 7 h, then cooled to 5˜10° C. in ice-cold bath. To this solution, 5 N HCl aq (10 mL) was added and the resulting solution (pH value was ca.6) was concentrated. To the residue, 2-propanol (80 mL) was added. This solution was concentrated. To the residue, 2-propanol (80 mL) was added and it was concentrated again. The residue was diluted with EtOH (80 mL) and the mixture was stirred at room temperature for 2 h. It was filtered through a celite pad (5.0 g) to remove NaCl. The Celite pad was washed with EtOH (20 mL) and the combined filtrate was concentrated. To the residue, CH3CN (40 mL) was added and it was concentrated. During this procedure, the formation of white precipitate was noticed. To the residue CH3CN (40 mL) was added and the resulting suspension was stirred at room temperature for 2 h. This mixture was filtered and obtained solid was washed with CH3CN (10 mL), then dried under reduced pressure to give 4.1 g (65%) of the titled compound as white powder.

후처리

  1. temperaturecooled to 5˜10° C. in ice-cold bath
  2. concentrationthe resulting solution (pH value was ca.6) was concentrated
  3. additionTo the residue, 2-propanol (80 mL) was added
  4. concentrationThis solution was concentrated
  5. additionTo the residue, 2-propanol (80 mL) was added
  6. concentrationit was concentrated again
  7. additionThe residue was diluted with EtOH (80 mL)
  8. stirringthe mixture was stirred at room temperature for 2 h
  9. filtrationIt was filtered through a celite pad (5.0 g)
  10. customto remove NaCl
  11. washThe Celite pad was washed with EtOH (20 mL)
  12. concentrationthe combined filtrate was concentrated
  13. additionTo the residue, CH3CN (40 mL) was added
  14. concentrationit was concentrated
  15. additionTo the residue CH3CN (40 mL) was added
  16. stirringthe resulting suspension was stirred at room temperature for 2 h
  17. filtrationThis mixture was filtered
  18. customobtained solid
  19. washwas washed with CH3CN (10 mL)
  20. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-76557a90238a4b5ba1a7436990a1a7ba
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595329B2

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