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Acetic Acid → Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylate

HRID 455308
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 455308
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14]([N:17]([C:19]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[C:26]([O:33]S(C2C=CC(C)=CC=2)(=O)=O)=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2)[CH3:18])(=[O:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].CO.C(O)(=O)C>CN(C=O)C.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14]([N:17]([C:19]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[C:26]([OH:33])=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2)[CH3:18])(=[O:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 86667514Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Produkt 1

HCID 67109690Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylate
Ausbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate (Example 2.1; 8.68 mmol) was dissolved in DMF (17 ml) at 40° C. and transferred to a 33% solution of NaOMe in MeOH (4.1 ml; 21.7 mmol) over 1-2 min at 25° C. The resulting yellow homogenous mixture was heated to 50° C. Mixture was cooled to 25° C. over 15 min and aged at 25° C. for 15 min. Acetic acid (1 ml) was added over 1 min, then water was added. The slurry was aged for 30 min and filtered. The filter cake was washed with water, and dried to give the target compound in 61% yield.

Aufarbeitung

  1. temperatureMixture was cooled to 25° C. over 15 min
  2. waitThe slurry was aged for 30 min
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. customdried
  6. customto give the target compound in 61% yield

Quellen und Nachweise

ORD-Eintrag
ord-b47920a914b14048869584783a2b898b
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08497270B2

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