Acetic Acid → 3-(1-ethoxycarbonylnonylamino)-5-t-butoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1719126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719126
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[S:4][CH2:3]1.O=[C:23]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(O)(=O)C.[BH]C#N.[Na]>C(O)C>[CH2:27]([O:26][C:24]([CH:23]([NH:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[S:4][CH2:3]1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:25])[CH3:28]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 12750087Ethyl 2-oxodecanoateHCID 134545423-amino-5-t-butoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneHCID 131714321Sodium boron cyanide hydride

Produkt 1

HCID 202675763-(1-ethoxycarbonylnonylamino)-5-t-butoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

1.3 g of 3-amino-5-t-butoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 3.0 g of ethyl 2-ketodecanoate were dissolved in 10 ml of ethanol. After the addition of 0.3 ml of acetic acid, the resulting mixture was stirred for 3 hours. Then, a solution of 420 mg of sodium boron cyanide hydride in 7 ml of ethanol was added dropwise thereto. After this mixture was allowed to stand overnight, it was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. The solution was washed with water, dried and then concentrated. The residue was purified by silica gel column chromatography using a 7:1 mixture of benzene and ethyl acetate as the eluent. Thus, there was obtained 1.8 g of the desired compound in the form of an oily material.

Aufarbeitung

  1. waitto stand overnight
  2. concentrationit was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. additiona 7:1 mixture of benzene and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-835edb2ab3ce49f6b9b50ad7e09e8967
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04539150

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