Boc-L-Valine → 1-{1-(RS)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-3-methoxybenzyl-2-thiourea

HRID 1610902

Reaktionsgleichung

Reaktionsgleichung von HRID 1610902
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]=[C:8]=[S:9].Cl.Cl.C[CH:16]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH2:20][CH2:19][N:18]([CH2:31][CH:32](NC(=O)C2C=CC(C)=CC=2)[CH:33]([CH3:35])[CH3:34])[CH2:17]1.C([NH:53][C@H](C(O)=O)C(C)C)(OC(C)(C)C)=O>C(Cl)Cl>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[Cl:29])[CH2:22][N:21]1[CH2:20][CH2:19][N:18]([CH2:31][CH:32]([C:5]2([CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH2:4]2)[CH2:6][NH:7][C:8]([NH2:53])=[S:9])[CH:33]([CH3:35])[CH3:34])[CH2:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 83693Boc-L-ValineHCID 1265123-Methoxybenzyl isothiocyanateHCID 22257752n-{1(Rs)-[3-methyl-4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-4-methylbenzamide dihydrochloride salt

Produkt 1

HCID 865889801-{1-(RS)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-3-methoxybenzyl-2-thiourea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Methoxybenzyl isothiocyanate (22 mg, 0.12 mmol) was added to a solution of 1-(RS)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropylamine (40 mg, 0.12 mmol) [prepared as described in Example 1 by substituting L-N-BOC-valine with DL-N-BOC-valine] in methylene chloride (1.5 ml). The reaction mixture was stirred for 2 h and then concentrated. Purification by flash chromatography with 20:1 methylene chloride: methanol as the eluant gave 1-{1-(RS)-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]-2-methylpropyl}-3-methoxybenzyl-2-thiourea (18 mg) as a solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customPurification by flash chromatography with 20:1 methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-7b4ca1cb5ba84af6992b0116ef6e4208
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984637B2

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