3-Aminopropionitrile → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl)amide

HRID 24683

Reaktionsgleichung

Reaktionsgleichung von HRID 24683
[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:3]=1[C:4]([NH:6][C@H:7]([C:25](O)=[O:26])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH3:24])=[CH:11][CH:10]=1)=[O:5].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:52]([CH2:54][CH2:55][NH2:56])#[N:53]>CN(C=O)C.O.C(Cl)CCl>[C:52]([CH2:54][CH2:55][NH:56][C:25](=[O:26])[C@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH3:24])=[CH:13][CH:14]=1)[NH:6][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:31][CH:30]=[CH:29][C:28]=1[Cl:32])#[N:53]

Komponenten

8

Edukt 4

HCID 16473-AminopropionitrileHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9912743(S)-2-(2,6-Dichlorobenzamido)-3-(2',6'-dimethoxy-[1,1'-biphenyl]-4-yl)propanoic acid

Produkt 1

HCID 54074886N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine (0.17 g), HOBT (0.0.08 g), DIEA (0.19 mL) and 2-cyanoethylamine (0.03 mL) in DMF (5 mL) was stirred at room temperature under N2. EDC (0.14 g) was added after 10 min and the mixture was stirred at room temperature under N2. The mixture was diluted with water and extracted with EtOAc. The extract was washed successively with water, 1 N HCl, satd. NaHCO3 and brine, dried and evaporated to give 0.17 g of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl)amide. ESMS: m/z 526 (MH+).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe extract was washed successively with water, 1 N HCl
  3. dry with materialNaHCO3 and brine, dried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-aff3e8797c4c4264b4026d0d5839a616
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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