Methyl N-(triethylammoniosulfonyl)carbamate → Ethyl (4S)-2-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-4,5-dihydro-1,3-oxazole-4-carboxylate

HRID 479618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479618
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]([NH:21][C@@H:22]([CH2:28][OH:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=O)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>O1CCCC1>[C:15]([O:14][C:12](=[O:13])[CH2:11][C@H:10]([C:19]1[O:29][CH2:28][C@@H:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1)[CH2:9][CH2:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([CH3:16])([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 59909824tert-butyl(3R)-6-cyclohexyl-3-({[(1S)-2-ethoxy-1-(hydroxymethyl)-2-oxoethyl]amino}carbonyl)hexanoate

Produkt 1

HCID 59909855Ethyl (4S)-2-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl}-4,5-dihydro-1,3-oxazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (3R)-6-cyclohexyl-3-({[(1S)-2-ethoxy-1-(hydroxymethyl)-2-oxoethyl]amino}carbonyl)hexanoate (Preparation 30) (4.14 g, 10 mmol) in anhydrous tetrahydrofuran (40 ml) was treated with (methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt [Burgess Reagent] (2.62 g, 11 mmol) and the resulting mixture was heated under reflux under a nitrogen atmosphere for 1 hour. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of pentane:ethyl acetate (80:20) to (50:50) to afford the title compound as a colourless oil (3.10)

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a gradient system of pentane:ethyl acetate (80:20) to (50:50)

Quellen und Nachweise

ORD-Eintrag
ord-bb631c1fcf574fa2919653b767780a7d
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645993B2

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