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Sodium Azide → (3R,4S,5R)-3-Azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

HRID 1773017
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1773017
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C@H:9]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[C@H:8](OS(C)(=O)=O)[CH:7]=1)=[O:5])[CH3:2].[N-:27]=[N+:28]=[N-:29].[Na+]>CS(C)=O.CCOC(C)=O.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C@@H:9]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[C@H:8]([N:27]=[N+:28]=[N-:29])[CH:7]=1)=[O:5])[CH3:2]
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Komponenten

6

Edukt 2

HCID 33557Sodium AzideHCID 42643351(3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Produkt 1

HCID 86628951(3R,4S,5R)-3-Azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 1140
Toluene
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 43, product of the preceding experiment) was dissolved in DMSO. To the clear light yellow solution NaN3 was added at room temperature and the suspension was stirred for 3 hours. The orange solution was diluted with EtOAc and toluene and extracted 3 times with aqueous NaHCO3. The organic phase was separated, dried over Na2SO4, filtered and the combined filtrates evaporated in a rotary evaporator at 20° C./70-10 mbar. The remaining yellow oil was dissolved twice in toluene and evaporated in a rotary evaporator at 20° C./70-10 mbar to obtain the crude dry product (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester (44), as yellow oil which was used in purification. A sample of 4 was obtained from crude 44 via a silica column chromatography using a 1:2 mixture of EtOAc and n-hexane. The combined fractions were evaporated and dried on a rotary evaporator to obtain 44 as a pale yellow oil.

Aufarbeitung

  1. extractionextracted 3 times with aqueous NaHCO3
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe combined filtrates evaporated in a rotary evaporator at 20° C./70-10 mbar
  6. dissolutionThe remaining yellow oil was dissolved twice in toluene
  7. customevaporated in a rotary evaporator at 20° C./70-10 mbar

Quellen und Nachweise

ORD-Eintrag
ord-165694da6fb94f0f9c440adcf4c46b21
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09250238B2

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