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

HRID 1250532

Reaktionsgleichung

Reaktionsgleichung von HRID 1250532
[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.[Cl:15][C:16]1[CH:17]=[C:18]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][C@@H:27](NC(=O)C2C=CC(C)=CC=2)[CH:28]([CH3:30])[CH3:29])[CH2:22][CH2:21]1.C([NH:52][C@H](C(O)=O)C(C)C)(OC(C)(C)C)=O>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[C:18]([CH:41]=[CH:42][C:43]=1[Cl:44])[CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH:27]([C:5]2([CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH2:4]2)[CH2:6][NH:7][C:8]([NH2:52])=[S:9])[CH:28]([CH3:30])[CH3:29])[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 83693Boc-L-ValineHCID 1265123-Methoxybenzyl isothiocyanateHCID 9958340n-{1 (s)-[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-4dd00b54e34a4693a58e485d52974d3f
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339087B1

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