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Hydrochloric Acid → tert-Butyl (2S)-1-oxo-1-(2-(tetrahydro-2H-pyran-3-ylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

HRID 525039
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525039
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH2:14])[CH2:9]1.Cl.[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH3:37])[C:25]([NH:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](OC)=[O:34])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C[Al](C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[O:26]=[C:25]([NH:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](=[O:34])[NH:14][CH:10]1[CH2:11][CH2:12][CH2:13][O:8][CH2:9]1)[C@@H:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:37]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 5200320Oxan-3-amineHCID 16682925TrimethylaluminumHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 86722058tert-Butyl (2S)-1-oxo-1-(2-(tetrahydro-2H-pyran-3-ylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel3×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Anhydrous triethylamine (600 μl, 4.31 mmols) was added to a solution of tetrahydro-2H-pyran-3-amine.HCl (600 mg, 4.36 mmols) in toluene (10 ml) and it was stirred at room temperature for 30 min. A solution of (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (900 mg, 2.90 mmols) in toluene (36 ml) and a 2M solution of trimethylaluminium in toluene (7 ml, 14 mmols) were added. The solution obtained was stirred at 80° C. for 2 h. Water (70 ml) and a 0.5M sodium tartrate solution (35 ml) were added. It was extracted with ethylacetate. The combined organic layers were washed with water and brine. It was dried, filtered and concentrated in vacuum. The title compound was obtained (750 mg, 68%).

Aufarbeitung

  1. customThe solution obtained
  2. extractionIt was extracted with ethylacetate
  3. washThe combined organic layers were washed with water and brine
  4. customIt was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4f3c9e4f3b6c45da880bdcf15a7164fb
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340547B2

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