2-Tetralone → HCID 11705519, Verbindung

HRID 131653

Reaktionsgleichung

Reaktionsgleichung von HRID 131653
Cl.[CH3:2][O:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH2:21])[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9].[CH2:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][C:26]1=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:2][O:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH:21][CH:31]2[CH2:32][CH2:33][C:34]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30]2)[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9].[OH:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH:21][CH:31]2[CH2:32][CH2:33][C:34]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30]2)[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9]

Komponenten

6

Edukt 3

HCID 682662-TetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 1317269182-(S)-amino-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt

Produkt 2

HCID 11705519HCID 11705519, VerbindungHCID 11712247HCID 11712247, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-(S)-amino-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt (600 mg, 1.59 mmol) and 2-tetralone (253 mg, 2.07 mmol) in dichloroethane was stirred at room temperature overnight. Sodium triacetoxyborohydride (530 mg, 2.5 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was quenched with water, adjusted pH to around 10 and extracted with methylene chloride. The organic layer was concentrated to dryness. The residue was purified by SCX column after eluting with 1 M NH3/methanol and concentrated to dryness to give 620 mg that was purified by Shimadzu HPLC to give 2-(S)-(1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide, LC-MS RT=2.2 min, M+1=472.5 as an oil and 2-(S)-(1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide, retention time, LC-MS RT=1.9 min, M+1=458.4 as a beige glass form.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe mixture was quenched with water
  3. extractionextracted with methylene chloride
  4. concentrationThe organic layer was concentrated to dryness
  5. customThe residue was purified by SCX column
  6. washafter eluting with 1 M NH3/methanol
  7. concentrationconcentrated to dryness
  8. customto give 620 mg that
  9. customwas purified by Shimadzu HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a1b977cb52b647f28a1188fb5c56bd23
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384968B2

Verknüpfte Notizen

Wird geladen…