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Ammonia → HCID 69330037, Verbindung

HRID 2299621
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2299621
[OH:1][C:2]1[CH:38]=[CH:37][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([N:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:12][C@H:13]([O:22][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][C:4]=2[CH:3]=1.[N:39]1[CH:44]=CC=CC=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:47].N>ClCCl.CN(C)C1C=CN=CC=1.C(O)C.O>[O:15]([CH2:14][C@@H:13]([O:22][Si:23]([CH2:26][CH3:27])([CH2:24][CH3:25])[CH2:28][CH3:29])[CH2:12][N:11]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH:9]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:37]=[CH:38][C:2]([O:1][C:44](=[O:47])[NH2:39])=[CH:3][C:4]=2[CH2:10]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 222AmmoniaHCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 57157362HCID 57157362, Verbindung

Produkt 1

HCID 69330037HCID 69330037, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under nitrogen, to a solution of N-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-tert-butoxycarbonylamine (150 mg) in dichloromethane (5 ml) were added pyridine (64 ml), 4-nitrophenyl chloroformate (116 mg) and a catalytic amount of 4-dimethylaminopyridine at 5° C. After being stirred at the same temperature for 2 hours, to this one was added about 6.8M ammonia in ethanol (0.5 ml), and the mixture was stirred at room temperature for 12 hours. The resulting mixture was pured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give N-[(2S)-3-phenoxy-2-(triethyl-silyloxy)propyl]-N-[3-carbamoyloxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]-tert-butoxycarbonylamine (129 mg).

Aufarbeitung

  1. customat 5° C
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-4e96b4e991bc4d8dbf6ed6f88a55dcf6
Quelldatensatz
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06495546B1

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