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Hydrochloric Acid → glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide hydrochloride

HRID 53089
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 53089
[C:1]1([CH2:7][O:8][C:9]([N:11]([CH2:13][C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:38])[CH2:21][NH:22]C(=O)[C@H](CC(C)C)NC(OC(C)(C)C)=O)=[O:15])[CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(COC(N(CC(NCCNC(=O)CNC(OC(C)(C)C)=O)=O)C)=O)C=CC=CC=1.[ClH:69].O>ClCCl>[ClH:69].[C:1]1([CH2:7][O:8][C:9]([N:11]([CH2:13][C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:38])[CH2:21][NH2:22])=[O:15])[CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 67628369HCID 67628369, VerbindungHCID 131719971HCID 131719971, Verbindung

Produkt 1

HCID 19961349glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

N-(N-(1,1-Dimethylethoxycarbonyl)leucyl)glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide. N-(1,1-Dimethylethoxycarbonyl)glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide (5.22 g, 8 mmol) was treated with excess hydrogen chloride in dichloromethane (50 mL) for 1 h. Water (50 mL) was added and the mixture was stirred vigorously for 15 min. The solvent and excess reagent were evaporated from the aqueous layer under reduced pressure to give crude glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide hydrochloride as a white solid. This material was stirred with N,N-diisopropylethylamine (3.231 g, 25 mmol) and N-(1,1-dimethylethoxycarbonyl)leucine 2,4,5-trichlorophenyl ester (3.19 g, 7.8 mmol) (Example II, Intermediate A) in dimethylformamide (30 mL) for 3 d. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and was washed with aqueous sodium hydroxide (5%), aqueous sulphuric acid (10%) and water and was dried with anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure gave N-(N-(1,1-dimethylethoxycarbonyl)leucyl)glycine N-(2-(N-(phenylmethoxycarbonyl)sarcosylamino)ethyl)amide (3.26 g, 78%).

Aufarbeitung

  1. customThe solvent and excess reagent were evaporated from the aqueous layer under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-733410222e30474ab661df595a04538d
Quelldatensatz
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05618528

Notizen zur Reaktion

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