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5'-(4-Iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester → 5'-(4-Iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid

HRID 2190578
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2190578
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:28])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([I:26])=[C:22]([CH3:27])[CH:21]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C>C1COCC1.O>[I:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([N:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]3)=[N:13][CH:14]=2)=[O:28])=[CH:21][C:22]=1[CH3:27]
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Komponenten

4

Edukt 1

HCID 593181915'-(4-Iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid ethyl ester

Produkt 1

HCID 593179955'-(4-Iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acidAusbeute 38,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5′-(4-iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester (200 mg, 0.39 mmol) in THF (10 mL) and H2O (2 mL) was treated with LiOH monohydrate (33 mg, 0.78 mmol). The mixture was stirred at room temperature for 24 h and then partitioned between EtOAc and H2O. The acidity of the water layer was adjusted to pH 5 by the addition of aqueous conc. HCl and solid Na2CO3. The water layer was separated and extracted once more with EtOAc. The EtOAc layers were combined, dried over Na2SO4, filtered and concentrated. The solid residue was suspended in CH2Cl2 then filtered and dried to afford the product (70 mg, Yield: 38%). HRMS m/z calcd for C19H20N3O3I [M+H]+: 466.0622. Found: 466.0619.

Aufarbeitung

  1. custompartitioned between EtOAc and H2O
  2. additionThe acidity of the water layer was adjusted to pH 5 by the addition of aqueous conc. HCl and solid Na2CO3
  3. customThe water layer was separated
  4. extractionextracted once more with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationthen filtered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f2d7d3a6811e4972ae8e666e56f96ae2
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08324385B2

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