Glycine, N-(3-nitrobenzoyl)- → N-[2-[[(3-nitrophenyl)carbonyl]amino]-1-oxoethyl]-beta-alanine, ethyl ester

HRID 378114

Reaktionsgleichung

Reaktionsgleichung von HRID 378114
C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)C1.[N+:19]([C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][CH:34]=1)[C:25]([NH:27][CH2:28][C:29]([OH:31])=O)=[O:26])([O-:21])=[O:20].Cl.[CH2:36]([O:38][C:39](=[O:43])[CH2:40][CH2:41][NH2:42])[CH3:37]>CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>[N+:19]([C:22]1[CH:23]=[C:24]([C:25]([NH:27][CH2:28][C:29]([NH:42][CH2:41][CH2:40][C:39]([O:38][CH2:36][CH3:37])=[O:43])=[O:31])=[O:26])[CH:32]=[CH:33][CH:34]=1)([O-:21])=[O:20]

Komponenten

6

Edukt 3

HCID 94858Glycine, N-(3-nitrobenzoyl)-HCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 676246Di(succinimido) carbonate

Produkt 1

HCID 20745455N-[2-[[(3-nitrophenyl)carbonyl]amino]-1-oxoethyl]-beta-alanine, ethyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

N,N'-Disuccinimidyl carbonate (14 g, 5.5 mmol) was added to 3-nitrobenzoyl glycine (10 g, 4.5 mmol) of Example BB in dry dimethylformamide (30 mL) followed by N,N-dimethylaminopyridine (200 mg). After a period of 1 hour beta-alanine ethyl ester hydrochloride (7 g, 4.6 mmol) in 20% aqueous potassium carbonate (50 mL) was added in one portion. After complete reaction the product was collected by filtration (14 g, 97% yield). 1H-NMR (d6 -DMSO) δ, 1.18 (t, 3H, J=7.2 Hz), 2.46 (t, 2H, J=7.0), 3.34 (q, 2H, J1 =6.7 Hz, J2 =12.6 Hz), 3.87 (d, 2H, J=5.9 Hz), 4.05 (q, 2H, J1 =7.4 Hz, J2 =14.2 Hz), 7.8 (t, 1H, J=8.0 Hz), 8.1 (t, 1H, J=5.6 Hz), 8.35 (m, 2H), 8.71 (s, 1H), 9.22 (bs, 1H).

Aufarbeitung

  1. customAfter complete reaction the product
  2. filtrationwas collected by filtration (14 g, 97% yield)

Quellen und Nachweise

ORD-Eintrag
ord-1ad9e99276204fa9a22f72084a62afcc
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028223

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