StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triphenylphosphine → allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methyl-2-[3-methyl-2,2-dioxo-5-(2-triethylsilanyloxy-ethyl)-2,3-dihydro-2-thia-1,3-diaza-phenalen-1-ylmethyl]-carbapen-2-em-3-carboxylate

HRID 1385899
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1385899
[CH2:1]([O:4][C:5]([O:7][C@@H:8]([C@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[C:14]([CH2:17]O)[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=[O:6])[CH:2]=[CH2:3].[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:46]=[S:47]1(=[O:70])[NH:58][C:57]2[C:59]3[C:53]([CH:54]=[C:55]([CH2:60][CH2:61][O:62][Si:63]([CH2:68][CH3:69])([CH2:66][CH3:67])[CH2:64][CH3:65])[CH:56]=2)=[CH:52][CH:51]=[CH:50][C:49]=3[NH:48]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]([O:7][C@@H:8]([C@H:10]1[C:25](=[O:26])[N:12]2[C:13]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[C:14]([CH2:17][N:48]3[C:49]4=[C:59]5[C:53](=[CH:52][CH:51]=[CH:50]4)[CH:54]=[C:55]([CH2:60][CH2:61][O:62][Si:63]([CH2:66][CH3:67])([CH2:64][CH3:65])[CH2:68][CH3:69])[CH:56]=[C:57]5[N:58]([CH3:27])[S:47]3(=[O:46])=[O:70])[C@H:15]([CH3:16])[C@H:11]12)[CH3:9])=[O:6])[CH:2]=[CH2:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11046746allyl (1S,5R,6S)-2-(hydroxymethyl)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methylcarbapen-2-em-3-carboxylateHCID 217162642,2-Dioxo-5-(2-triethylsilanyloxy-ethyl)-2,3-dihydro-2-thia-1,3-diaza-phenalene

Produkt 1

HCID 131722782
allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methyl-2-[3-methyl-2,2-dioxo-5-(2-triethylsilanyloxy-ethyl)-2,3-dihydro-2-thia-1,3-diaza-phenalen-1-ylmethyl]-carbapen-2-em-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-2-hydroxymethyl-1-methyl-carbapen-2-em-3-carboxylate (365 mg, 1.0 mmol), triphenylphosphine (315 mg, 1.2 mmol), and 2,2-dioxo-5-(2-triethylsilanyloxy-ethyl)-2,3-dihydro-2-thia-1,3-diaza-phenalene (432 mg, 1.1 mmol) in anhydrous tetrahydrofuran (7 mL) is cooled in an ice-bath and stirred under a nitrogen atmosphere while diisopropyl azodicarboxylate (0.24 mL, 1.2 mmol) is added dropwise over a few minutes. The resulting solution is stirred in the cold for 30 minutes, then diluted with chloroform, washed with 5% aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered and evaporated under vacuum. The residue is purified by silica gel flash chromatography, eluting with hexane-ethyl acetate, to afford allyl (1S,5R,6S)-6-[1(R)-allyloxycarbonyloxy-ethyl]-1-methyl-2-[3-methyl-2,2-dioxo-5-(2-triethylsilanyloxy-ethyl)-2,3-dihydro-2-thia-1,3-diaza-phenalen-1-ylmethyl]-carbapen-2-em-3-carboxylate.

Aufarbeitung

  1. additionis added dropwise over a few minutes
  2. washwashed with 5% aqueous sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue is purified by silica gel flash chromatography
  7. washeluting with hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b77933ea10344a9f9f3d05573c011bb0
Quelldatensatz
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06265395B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion