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4-Methylmorpholine → 3-Tert-butoxycarbonyl-5(S)-{2-[N-(1-carbamoyl-1-methyl-ethyl)-carbamoyl]-2(S)-isopropyl-ethyl}-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine

HRID 744841
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 744841
CN1CCOCC1.Cl.[NH2:9][C:10]([CH3:15])([CH3:14])[C:11]([NH2:13])=[O:12].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:40]([O:44][C:45]([N:47]1[C@@H:51]([CH2:52][C@@H:53]([CH:69]([CH3:71])[CH3:70])[CH2:54][C:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[C:57]([O:63][CH2:64][CH2:65][CH2:66][O:67][CH3:68])[CH:56]=2)[C@H:50]([CH2:72][C@H:73]([C:77](O)=[O:78])[CH:74]([CH3:76])[CH3:75])[O:49][C:48]1([CH3:81])[CH3:80])=[O:46])([CH3:43])([CH3:42])[CH3:41]>CN(C)C=O>[C:40]([O:44][C:45]([N:47]1[C@@H:51]([CH2:52][C@@H:53]([CH:69]([CH3:71])[CH3:70])[CH2:54][C:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[C:57]([O:63][CH2:64][CH2:65][CH2:66][O:67][CH3:68])[CH:56]=2)[C@H:50]([CH2:72][C@H:73]([C:77](=[O:78])[NH:9][C:10]([C:11](=[O:12])[NH2:13])([CH3:15])[CH3:14])[CH:74]([CH3:75])[CH3:76])[O:49][C:48]1([CH3:80])[CH3:81])=[O:46])([CH3:43])([CH3:42])[CH3:41]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145690092-Amino-2-methylpropanamide hydrochlorideHCID 236254795-Oxazolidinepropanoic acid, 3-[(1,1-dimethylethoxy)carbonyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-alpha-(1-methylethyl)-, (alphaS,4S,5S)-

Produkt 1

HCID 22865784
3-Tert-butoxycarbonyl-5(S)-{2-[N-(1-carbamoyl-1-methyl-ethyl)-carbamoyl]-2(S)-isopropyl-ethyl}-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

106 μl of 4-methyl-morpholine, 66 mg of 2-aminoisobutyric acid amide hydrochloride and 91 mg of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU) are added in succession to 119 mg of 3-tert-butoxycarbonyl-5(S)-(2(S)-carboxy-3-methyl-butyl)-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine (Example 124c) in 8 ml of dimethylformamide. The reaction mixture is stirred for 8 days at 40° C. The mixture is concentrated by evaporation and the residue is partitioned between ethyl acetate and saturated sodium chloride solution. The organic phases are concentrated by evaporation and the residue is purified by means of FC (60 g of silica gel, dichloromethane/methanol=95:5). The title compound is obtained: Rf (dichloromethane/methanol=95:5)=0.30.

Aufarbeitung

  1. concentrationThe mixture is concentrated by evaporation
  2. customthe residue is partitioned between ethyl acetate and saturated sodium chloride solution
  3. concentrationThe organic phases are concentrated by evaporation
  4. customthe residue is purified by means of FC (60 g of silica gel, dichloromethane/methanol=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-1a69636e059e465fbe9a9d14f27b186e
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05559111

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