Triethylamine → HCID 178522622, Verbindung

HRID 255131

Reaktionsgleichung

Reaktionsgleichung von HRID 255131
Cl.[NH2:2][C:3]1[S:4][C:5]([Cl:8])=[CH:6][N:7]=1.CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[OH:38][C:39]12[CH2:48][CH:43]3[CH2:44][CH:45]([CH2:47][C:41]([C:49](O)=[O:50])([CH2:42]3)[CH2:40]1)[CH2:46]2>O1CCCC1.C(OCC)(=O)C>[Cl:8][C:5]1[S:4]/[C:3](=[N:2]\[C:49]([C:41]23[CH2:42][CH:43]4[CH2:44][CH:45]([CH2:46][C:39]([OH:38])([CH2:48]4)[CH2:40]2)[CH2:47]3)=[O:50])/[NH:7][CH:6]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27365183-Hydroxyadamantane-1-carboxylic acid

Produkt 1

HCID 178522622HCID 178522622, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 2-amino-5-chlorothiazole hydrochloride (Aldrich) (1.00 g, 5.84 mmol) in tetrahydrofuran (50 mL) was added N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (1.12 g, 5.84 mmol), 1-hydroxybenzotriazole (0.79 g, 5.84 mmol), triethylamine (2.04 mL, 14.6 mmol), and 3-hydroxyadamantane-1-carboxylic acid (Acros) (1.15 g, 5.84 mmol). The mixture was stirred overnight at room temperature and was diluted with ethyl acetate, washed with 1 M aqueous sodium carbonate, dried (Na2SO4), filtered and concentrated. Purification by column chromatography (SiO2) using a gradient of 0% to 100% ethyl acetate:hexane provided the title compound. MS (ESI+) m/z 313 (M+H)+.

Aufarbeitung

  1. washwashed with 1 M aqueous sodium carbonate
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-8e7dc3c110a84eb9a7a8bd4dbd8cb2bc
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875639B2

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