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Trifluoroacetic acid → 2-Amino-N-((2R)-3-(benzyloxy)-1-(7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-1-oxopropan-2-yl)-2-methylpropanamide

HRID 1036703
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1036703
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:30][C:31](=[O:43])[C:32]([NH:35]C(=O)OC(C)(C)C)([CH3:34])[CH3:33])[C:11]([N:13]1[CH2:17][CH2:16][C:15]2([CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:20][N:19]([CH3:28])[C:18]2=[O:29])[CH2:14]1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[NH2:35][C:32]([CH3:34])([CH3:33])[C:31]([NH:30][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:11]([N:13]1[CH2:17][CH2:16][C:15]2([CH:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][N:19]([CH3:28])[C:18]2=[O:29])[CH2:14]1)=[O:12])=[O:43]
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Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 71060634tert-Butyl 1-((2R)-3-(benzyloxy)-1-(7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate

Produkt 1

HCID 710605682-Amino-N-((2R)-3-(benzyloxy)-1-(7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-1-oxopropan-2-yl)-2-methylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
2×
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 1-((2R)-3-(benzyloxy)-1-(7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (step 3) (206.5 mg) in DCM (4 mL) was treated with TFA (537 uL, 6.97 mmol). The reaction mixture was stirred at room temperature for 2 days. A further portion of TFA (2 ml) was added and stirring continued for 20 minutes. The mixture was concentrated in vacuo to afford a colourless oil. The oil was dissolved in MeOH and applied to a 10 g pre-wetted (MeOH) SCX-2 cartridge. The column was washed with MeOH (70 mL) and the product was eluted with 2M NH3 in MeOH (70 mL). The clean fractions were concentrated in vacuo to afford a colourless oil. The oil was further purified by mass-directed LC-MS to afford the title compound;

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 20 minutes
  3. concentrationThe mixture was concentrated in vacuo
  4. customto afford a colourless oil
  5. washThe column was washed with MeOH (70 mL)
  6. washthe product was eluted with 2M NH3 in MeOH (70 mL)
  7. concentrationThe clean fractions were concentrated in vacuo
  8. customto afford a colourless oil
  9. customThe oil was further purified by mass-directed LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-701f6aca46004b9fa4836dcd91cb80fe
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546416B2

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