Triethylamine → methyl (2R)-2-[(t-butoxycarbonyl)amino]-4-oxo-4-[4-(9H-thioxanthen-9-ylidene)-1-piperidinyl]butanoate

HRID 2236036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236036
Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[CH:20]1[C:33]2[C:32](=[C:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[S:25][C:24]=2[CH:23]=[CH:22][CH:21]=1.[C:40]([O:44][C:45]([NH:47][C@H:48]([C:53]([O:55][CH3:56])=[O:54])[CH2:49][C:50](O)=[O:51])=[O:46])([CH3:43])([CH3:42])[CH3:41].[Cl-].[NH4+]>ClCCl>[C:40]([O:44][C:45]([NH:47][C@H:48]([CH2:49][C:50](=[O:51])[N:37]1[CH2:38][CH2:39][C:34](=[C:32]2[C:33]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[S:25][C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:35][CH2:36]1)[C:53]([O:55][CH3:56])=[O:54])=[O:46])([CH3:43])([CH3:42])[CH3:41]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11021202(3S)-3-(((tert-butoxy)carbonyl)amino)-4-methoxy-4-oxobutanoic acidHCID 130525974-(9H-thioxanthen-9-ylidene)piperidine

Produkt 1

HCID 86594136methyl (2R)-2-[(t-butoxycarbonyl)amino]-4-oxo-4-[4-(9H-thioxanthen-9-ylidene)-1-piperidinyl]butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.00 g (5.22 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride, 0.73 ml (5.24 mmol) of triethylamine and 1.351 g (4.84 mmol) of 4-(9H-thioxanthen-9-ylidene)piperidine were added to 1.290 g (5.22 mmol) of (S)-3-[(t-butoxycarbonyl)amino]-4-methoxy-4-oxobutanoic acid in 20 ml of dichloromethane in an ice bath, and they were stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was added to the reaction mixture. After extracting with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=7:3 to 1:1) to obtain the title compound.

Aufarbeitung

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=7:3 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4f231160c4ce47308b8a5323c181bc52
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713957B2

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