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Dichloromethane → (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid methylamide

HRID 377076
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 377076
ClCCl.[O:4]1[C@@:21]2([CH3:22])[C@@H:5]1[CH2:6][C@@H:7]1[C:12]([C:13](O)=[O:14])=[CH:11][O:10][C@@H:9]([O:16][C:17](=[O:20])[NH:18][CH3:19])[C@H:8]12.[N-]=[N+]=[N-].C1(OP([O-])(OC2C=CC=CC=2)=O)C=CC=CC=1.Cl.[CH3:44][NH2:45]>ClCCl.CO.C(N(CC)CC)C>[CH3:44][NH:45][C:13]([C:12]1[C@H:7]2[CH2:6][C@@H:5]3[O:4][C@:21]3([CH3:22])[C@@H:8]2[C@H:9]([O:16][C:17](=[O:20])[NH:18][CH3:19])[O:10][CH:11]=1)=[O:14]
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Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 6364545Methylamine hydrochlorideHCID 18397301(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acidHCID 21964642Diphenylphosphate azide

Produkt 1

HCID 57278225
(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid methylamide
Ausbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

A dichloromethane solution containing 395 mg of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid described in Example 1 was cooled with ice followed by addition of 0.49 ml of triethylamine, 0.38 ml of diphenylphosphate azide and 118 mg of methylamine hydrochloride and stirring for 15 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with dilute hydrochloric acid, saturated aqueous sodium bicarbonate and brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain colorless needles from the dichloromethane-methanol eluate in the form of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid methylamide (194 mg, yield: 47%). The physicochemical properties of this compound are described in Table 3, Compound No. 15.

Aufarbeitung

  1. temperaturewas cooled with ice
  2. extractionThe reaction mixture was then extracted with dichloromethane
  3. washAfter washing the organic phase with dilute hydrochloric acid, saturated aqueous sodium bicarbonate and brine, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-713a7597141f40f58c7ad370f495c26f
Quelldatensatz
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06022888

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