Triethylamine → Tert-butyl 9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]-undecane-4-carboxylate

HRID 2284865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284865
Cl.C1[C:7]2(C[CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)CNCC1.[CH2:20]([NH:24][C:25]([NH:27][CH2:28][C:29]([OH:31])=O)=[O:26])[CH:21]([CH3:23])[CH3:22].C(N(CC)CC)C.CN(C(ON1N=N[C:49]2[CH:50]=[CH:51][CH:52]=[N:53][C:48]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.C(OCC)(=O)C.CN(C)C=O>[CH2:20]([NH:24][C:25]([NH:27][CH2:28][C:29]([N:53]1[CH2:48][CH2:49][C:50]2([CH2:7][CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:11]2)[CH2:51][CH2:52]1)=[O:31])=[O:26])[CH:21]([CH3:22])[CH3:23]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16785937(Isobutylcarbamoyl)glycineHCID 71464197Tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

Produkt 1

HCID 118022279Tert-butyl 9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]-undecane-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a round bottom flask add tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (1.38 mmol), 2-(isobutylcarbamoylamino)acetic acid (1.15 mmol), dimethylformamide (3.8 mL), triethylamine (1.72 mmol) and HATU (1.26 mmol. Stir at room temperature for 16 hours, then dilute with water (50 mL) and ethyl acetate (50 mL). Wash the organic phase with concentrated ammonium chloride (50 mL) and brine (50 mL). Dry the organics over sodium sulfate, filter, and concentrate under reduced pressure. Purify the intermediate by flash chromatography (40 g silica gel cartridge) eluting with 0-10% methanol in ethyl acetate to yield tert-butyl 9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]undecane-4-carboxylate (0.38 g, 0.93 mmol): MS (m/z): 411.2 (M+H).

Aufarbeitung

  1. washWash the organic phase with concentrated ammonium chloride (50 mL) and brine (50 mL)
  2. dry with materialDry the organics over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify the intermediate by flash chromatography (40 g silica gel cartridge)
  6. washeluting with 0-10% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f0b629ee13954bd28965925c3b5605b4
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145437B2

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