2-Tetralone → 2-(S)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide

HRID 131657

Reaktionsgleichung

Reaktionsgleichung von HRID 131657
[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:16])[C@@H:11]([NH2:15])[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][C:18]1=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:16])[C@@H:11]([NH:15][CH:23]2[CH2:24][CH2:25][C:26]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:22]2)[CH2:12][CH2:13][CH3:14])=[N:6][CH:5]=1)([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 682662-TetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 86604587HCID 86604587, Verbindung

Produkt 1

HCID 116104112-(S)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-(S)-amino-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide (350 mg, 1.4 mmol) and 2-tetralone (318 mg, 2.2 mmol)in 20 mL of methylene chloride and 5 drops of acetic acid was treated with sodium triacetoxyborohydride (462 mg, 2.2 mmol) and stirred at room temperature overnight. The mixture was concentrated and eluted through SPEC SCX cartridge and concentrated to dryness. The residue was purified by silica gel column chromatography to give 2-(S)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide as a solid, LC-MS, RT=1.9 min, M+1=372.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. washeluted through SPEC SCX cartridge
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e16c27bbe9224dc3992a6a93e3689b5c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384968B2

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