Dimethylformamide → Benzo[b]thiophene-2-carboxylic acid [1-(2-phenyl-1(r)-{2-[4-(thiophen-2-yl-acetyl)-piperazin-1-yl]-ethylcarbamoyl}-ethylcarbamoyl)-cyclopentyl]-amide

HRID 917303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917303
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:12][C:13]([O:15]CC2C=CC=CC=2)=O)[C:9]([OH:11])=O)=[CH:3][CH:2]=1.C([N:30]1[CH2:35][CH2:34][N:33]([CH2:36]CO)[CH2:32]C1)(OC(C)(C)C)=O.[S:39]1[C:43]([C:44]2[O:48]C(=O)[C:46]3([CH2:53][CH2:52][CH2:51][CH2:50]3)[N:45]=2)=[CH:42][C:41]2[CH:54]=[CH:55][CH:56]=[CH:57][C:40]1=2.[CH3:58][N:59]([CH:61]=[O:62])[CH3:60]>C(Cl)Cl>[C:4]1([CH2:7][C@@H:8]([NH:12][C:13]([C:46]2([NH:45][C:44]([C:43]3[S:39][C:40]4[CH:57]=[CH:56][CH:55]=[CH:54][C:41]=4[CH:42]=3)=[O:48])[CH2:50][CH2:51][CH2:52][CH2:53]2)=[O:15])[C:9](=[O:11])[NH:30][CH2:35][CH2:34][N:33]2[CH2:32][CH2:60][N:59]([C:61](=[O:62])[CH2:57][C:40]3[S:39][CH:43]=[CH:42][CH:41]=3)[CH2:58][CH2:36]2)[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylateHCID 179796172-Benzo[b]thiophen-2-yl-3-oxa-1-azaspiro[4.4]-non-1-en-4-one

Produkt 1

HCID 10233505Benzo[b]thiophene-2-carboxylic acid [1-(2-phenyl-1(r)-{2-[4-(thiophen-2-yl-acetyl)-piperazin-1-yl]-ethylcarbamoyl}-ethylcarbamoyl)-cyclopentyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Analogously to Example 95) 4-[2-2(R)-amino-3-phenyl-propionylamino)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (obtained starting from Z-D-phenylalanine and N-Boc-4-hydroxyethylpiperazine by reactions and couplings widely described in literature and in part already reported in previous examples) (100 mg, 0.26 mmol) and 2-benzo[b]thiophen-2-yl-3-oxa-1-azaspiro[4.4]-non-1-en-4-one (72 mg, 0.26 mmol) are caused to react in DMF to yield a product which is deprotected and subsequently acylated with thiophen-2-yl-acethyl chloride in CH2Cl2 (as described in Example 94 and purified by flash chromatography using AcOEt as the eluent. 69 mg (0.10 mmol) of benzo[b]thiophene-2-carboxylic acid [1-(2-phenyl-1(R)-{2-[4-(thiophen-2-yl-acetyl)-piperazin-1-yl]-ethylcarbamoyl}-ethylcarbamoyl)-cyclopentyl]-amide are so obtained.

Aufarbeitung

  1. customto yield a product which
  2. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c3137d8dd92b41baa88d8d5c6c393f40
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273856B2

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