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Hydrochloric Acid → (S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

HRID 2351086
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2351086
[OH:1][C:2]1[C:3](=[O:18])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][NH:13][C:12]2=[O:17])=[O:9])[NH:6][CH:7]=1.CN([Si](C)(C)C)C(=O)C(F)(F)F.N1CCCNC1=O.[O:38]=[C:39]1[C@@H:42]([NH:43][C:44](=[O:53])[O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:41][NH:40]1.Cl[S:55]([N:58]=[C:59]=[O:60])(=[O:57])=[O:56].Cl>C(OCC)(=O)C.ClCCl>[OH:1][C:2]1[C:3](=[O:18])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:55]([NH:58][C:59]([N:40]3[CH2:41][C@H:42]([NH:43][C:44](=[O:53])[O:45][CH2:46][C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:39]3=[O:38])=[O:60])(=[O:57])=[O:56])[C:12]2=[O:17])=[O:9])[NH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 70918Chlorosulfonyl isocyanateHCID 746152(1H)-Pyrimidinone, tetrahydro-2×HCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 198480131,4-Dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide

Produkt 1

HCID 86743424(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2.73 g (10.82 mmol) 1,4-dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide and 8.63 g (43.29 mmol) N-methyl-N-trimethylsilyltrifluoroacetamide were dissolved in ethyl acetate and stirred for 1 hour (solution A). To a suspension of 2.38 g (10.82 mmol) (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 80 ml ethyl acetate was added 1.53 g (10.82 mmol) chlorosulfonyl isocyanate. After stirring for 1 hour, the solution was cooled to 0° C. and 9 ml dichloromethane and subsequently solution A were added. After stirring overnight at room temperature ice water was added and the pH was adjusted to 1.3 with 3N hydrochloric acid. The precipitate was filtered off, washed with water, dried in vacuo and slurried with ether. Yield 4.95 g, melting range 150°-230° C. (dec.).

Aufarbeitung

  1. additionwas added
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d6b1ec5eeed344889ebecb40d77e4209
Quelldatensatz
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04871841

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