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Hydrochloric Acid → HCID 20622811, Verbindung

HRID 2121220
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2121220
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[CH:6][C:5]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Li+].Cl.Cl.[CH3:30][O:31][C:32](=[O:39])[C@H:33]([CH2:35][CH2:36][S:37][CH3:38])[NH2:34].ON1C(=O)C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CO.C(OCC)(=O)C.N1C=CC=CC=1.C1COCC1>[CH3:30][O:31][C:32](=[O:39])[C@H:33]([CH2:35][CH2:36][S:37][CH3:38])[NH:34][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[CH:6][C:5]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 54568565HCID 54568565, Verbindung

Produkt 1

HCID 20622811HCID 20622811, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of the product of Example 280B (446 mg, 1.3 mmol) and aqueous saturated lithium hydroxide (3 mL) in methanol (5 mL) was heated at 60° C. for 15 hours. The reaction mixture was then neutralized with hydrogen chloride (4 N in dioxane, 5 mL). The reaction mixture was concentrated in vacuo to dryness. To the residue was added sequentially L-methionine methyl ester hydrochloride (311 mg, 1.56 mmol), 3-hydroxy 1,2,3-benzotriazin-4(3H)-one (318 mg, 1.95 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodimide (374 mg, 1.95 mmol), THF (10 mL) and pyridine (1 mL). After 15 hours, the reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was then purified by column chromatography (ethyl acetate) to give the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by column chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d30f093b1e4c4bffbabaa70415dca66f
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06693123B2

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