Triethylamine → 2-(2-Hydroxy-3-methyl-butyrylamino)-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide

HRID 852343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852343
[OH:1][C@@H:2]([CH:6]([CH3:8])[CH3:7])[C:3](O)=[O:4].[C:9]([C:13]1[S:17][C:16]([NH:18][C:19](=[O:25])[CH:20]([NH2:24])[CH2:21][CH2:22][CH3:23])=[N:15][N:14]=1)([CH3:12])([CH3:11])[CH3:10].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>C(Cl)Cl>[C:9]([C:13]1[S:17][C:16]([NH:18][C:19](=[O:25])[CH:20]([NH:24][C:3](=[O:4])[CH:2]([OH:1])[CH:6]([CH3:8])[CH3:7])[CH2:21][CH2:22][CH3:23])=[N:15][N:14]=1)([CH3:11])([CH3:10])[CH3:12]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 853180(S)-2-Hydroxy-3-methylbutanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 860331642-Amino-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide

Produkt 1

HCID 116101072-(2-Hydroxy-3-methyl-butyrylamino)-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-(S)-hydroxyl-3-methyl-butyric acid (35.4 mg, 0.3 mmol), 2-amino-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide (88 mg, 0.3 mmol), HBOT (43 mg, 0.21 mmol), EDC HCl (69 mg, 0.36 mmol.) and triethylamine (0.17 ml) in 2 ml of methylene chloride was stirred at room temperature until product formation or disappearance of starting material. The mixture was quenched with water and extracted with methylene chloride. The organic layer was separated, washed with dilute HCl, brine, dried over sodium sulfate and the solvent was removed at reduced pressure to provide the title compound as a cude oil. The oil was purified by Shimadzu HPLC to provide the title compound as a light yellow solid (44 mg), LC-MS M+1=357.1

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. customThe organic layer was separated
  4. washwashed with dilute HCl, brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-feac8b54abc447ae8ec7e3c95e57ef45
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253195B2

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