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Methylamine → HCID 86654195, Verbindung

HRID 422167
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 422167
[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:24])[C@H:15]([CH2:16][S:17]2=[O:20])[C@:14]2([CH3:21])[C@H:9]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[CH:4][C:3]=1[C:25]([OH:27])=O.[CH3:28][N:29](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN>C1COCC1.CN(C=O)C.CCOC(C)=O>[OH:1][C:2]1[CH:19]=[C:18]2[C:5]([C@@:6]3([CH3:24])[C@H:15]([CH2:16][S:17]2=[O:20])[C@:14]2([CH3:21])[C@H:9]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]3)=[CH:4][C:3]=1[C:25]([NH:29][CH3:28])=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58294800(1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8-oxo-8lambda4-thiatetracyclo-[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4-carboxylic acid

Produkt 1

HCID 86654195
HCID 86654195, Verbindung
Ausbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8-oxo-8λ4-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4-carboxylic acid (71) (0.40 g, 1.1 mmol), HATU (0.49 g, 1.3 mmol), Hunig's base (0.24 mL, 1.4 mmol), methylamine (2 M in diethyl ether, 2.7 mL, 5.4 mmol) in anhydrous THF (10 mL) and DMF (2 mL) was placed in a sealed vessel. The reaction was stirred at room temperature for 18 h. The reaction was diluted with EtOAc and washed with water and brine. The organic layer was separated and concentrated to dryness. The crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 7:3) to yield (1R,10R,11S,16S)-5-hydroxy-N,1,11,15,15-pentamethyl-8-oxo-8λ4-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-4-carboxamide (72) (0.07 g, 16% yield) as a white solid.

Aufarbeitung

  1. customwas placed in a sealed vessel
  2. washwashed with water and brine
  3. customThe organic layer was separated
  4. concentrationconcentrated to dryness
  5. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-1b26392101a74af7b3ad53a94a2e1e6d
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08101605B2

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