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1,3-Oxazolidine → tert-Butyl (S)-6-tert-butoxycarbonylamino-2-[((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-ylsulfamoyl)amino]hexanoate

HRID 2274557
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2274557
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:21][S:22](N1CCOC1=O)(=[O:24])=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:31][C@@H:32]1[CH2:47][C:46]2=[CH:48][CH:49]=[C:43]([CH:44]=[CH:45]2)[O:42][CH2:41][CH2:40][CH2:39][CH2:38][O:37][CH2:36][C@H:35]([CH:50]([CH3:52])[CH3:51])[NH:34][C:33]1=[O:53].O1CCNC1>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:21][S:22](=[O:23])(=[O:24])[NH:31][C@@H:32]1[CH2:47][C:46]2=[CH:45][CH:44]=[C:43]([CH:49]=[CH:48]2)[O:42][CH2:41][CH2:40][CH2:39][CH2:38][O:37][CH2:36][C@H:35]([CH:50]([CH3:51])[CH3:52])[NH:34][C:33]1=[O:53])[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[O:7])([CH3:3])([CH3:2])[CH3:4]
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Komponenten

5

Edukt 3

HCID 5366831,3-OxazolidineHCID 58360483(9S,12R)-12-Amino-9-isopropyl-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-11-one2×HCID 67028806tert-butyl(S)-6-tert-butoxycarbonylamino-2-(2-oxooxazolidine-3-sulfonylamino)hexanoate

Produkt 1

HCID 67320439tert-Butyl (S)-6-tert-butoxycarbonylamino-2-[((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-ylsulfamoyl)amino]hexanoate
Ausbeute 14,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 387 mg (0.858 mmol) of tert-butyl (S)-6-tert-butoxycarbonylamino-2-(2-oxooxazolidine-3-sulfonylamino)hexanoate and 250 mg (0.780 mmol) of (9S,12R)-12-amino-9-isopropyl-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-11-one (compound 1-1E) in 15 ml of acetonitrile was stirred at 80° C. After 1 day (d), the same amount of the oxazolidine was again added, and the mixture was stirred for 1 d. The reaction mixture was then concentrated and the residue was purified by prep. HPLC. Product-containing fractions were combined, the acetonitrile was evaporated off, made slightly alkaline with sat. NaHCO3 solution and extracted several times with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and concentrated. 78 mg of the title compound were obtained.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by prep
  3. customthe acetonitrile was evaporated off
  4. extractionextracted several times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f4a4ddf023404e19aefe90417a722cec
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09126955B2

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