Acetic Acid → N-[2-[2-(4-Hydroxy-2-oxo-3H-benzothiazol-7-yl)ethylamino]ethyl]-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide

HRID 2234181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234181
O=[CH:2][CH2:3][N:4]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:5](=[O:17])[CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[NH2:33][CH2:34][CH2:35][C:36]1[C:44]2[S:43][C:42](=[O:45])[NH:41][C:40]=2[C:39]([OH:46])=[CH:38][CH:37]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[OH:46][C:39]1[C:40]2[NH:41][C:42](=[O:45])[S:43][C:44]=2[C:36]([CH2:35][CH2:34][NH:33][CH2:2][CH2:3][N:4]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:5](=[O:17])[CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:37][CH:38]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochlorideHCID 86625180N-(2-Oxoethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide

Produkt 1

HCID 16035070N-[2-[2-(4-Hydroxy-2-oxo-3H-benzothiazol-7-yl)ethylamino]ethyl]-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

N-(2-Oxoethyl)-3-phenethyloxy-N-(5-phenethyloxypentyl)propanamide (Example 9c), 0.12 g) was dissolved in methanol (5 mL) and treated with 7-(2-aminoethyl)-4-hydroxy-3H-benzothiazol-2-one hydrochloride (0.32 g), acetic acid (0.1 mL) and water (0.3 mL). The resultant mixture was stirred for 2 hours and then sodium cyanoborohydride (0.01 g) was added and the reaction mixture was stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in methanol (5 mL) and adsorbed onto silica gel. The product was purified by flash chromatography eluting with 5% methanol, 1% ammonia in dichloromethane. Collected fractions were concentrated and the resultant residue was taken up in dichloromethane (5 mL) and treated with 4N hydrogen chloride in dioxane (0.2 mL). The mixture was stirred vigorously and concentrated. The resulting gum was azeotroped with dichloromethane (3×5 mL) to give the titled compound (0.13 g) as a white solid.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe product was purified by flash chromatography
  3. washeluting with 5% methanol, 1% ammonia in dichloromethane
  4. concentrationCollected fractions were concentrated
  5. additiontreated with 4N hydrogen chloride in dioxane (0.2 mL)
  6. stirringThe mixture was stirred vigorously
  7. concentrationconcentrated
  8. customThe resulting gum was azeotroped with dichloromethane (3×5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-9bd2789dc74b4e079d95746dd87d6b81
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709511B2

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