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N-methyl-2-pyrrolidone → Acetic Anhydride

HRID 1066708
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1066708
N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:6]([OH:8])=[O:7])C(C)C.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H](C(O)=O)[CH2:28][C:29](=O)[NH:30][C:31]([C:44]1C=CC=CC=1)([C:38]1C=CC=CC=1)C1C=CC=CC=1.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:72](C(O)=O)[CH2:73]C1C=CC(CP(OCC)(OCC)=O)=CC=1.[CH3:109]N1[C:114](=[O:115])[CH2:113]CC1>>[C:6]([O:8][C:114](=[O:115])[CH3:113])(=[O:7])[CH3:2].[CH3:72][CH2:73][N:30]([CH:29]([CH3:28])[CH3:109])[CH:31]([CH3:38])[CH3:44]
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Komponenten

6

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 640248Fmoc-Asn(Trt)-OHHCID 688217FMOC-L-valine2×HCID 17040155(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-((diethoxyphosphoryl)methyl)phenyl)propanoic acid

Produkt 2

HCID 7918Acetic Anhydride
HCID 81531
Diisopropylethylamine

Versuchsvorschrift

Starting from 0.5 mmol of 4-(2′,4′-dimethoxyphenyl-Fmoc-aminomethyl)phenoxyacetamido-norleucyl-4-methylbenzhydrylamine-polystyrene resin (Rink MBHA) the phosphonomethylpeptide was assembled on the resin in analogous manner as described in the example 1, adding the protected amino acids in the following order: Fmoc—Val—OH, Fmoc—Asn(Trt)—OH, Fmoc—Val—OH, Fmoc—Phe(p—CH2PO3Et2)—OH. The N-terminal acetylation was obtained by treatment of the peptidyl resin with 5 eq of acetic anhydride and 5 eq of DIEA in NMP for 30 min at 25° C. The cleavage from the resin and the removal of the protecting groups, except the phosphonate ethyl groups, were carried out as described in example 1. The 270 mg of crude peptide were suspended in refluxing DCM with 1 mL of trimethylbromosilane for 2 h. After evaporation of the solvent the completely deprotected peptide was purified by RP—HPLC as described in Example 1 (but with acetonitrile gradient 5-43.5 %) giving the title compound with chromatographic purity (HPLC) of 98.0%. Amino acid ratios: Val 2 (2); Asx 1.3 (1). Peptide content: 100%. FAB mass spectroscopy: m/z 613 [MH]+. (MW 612.6).

Quellen und Nachweise

ORD-Eintrag
ord-6419e4dfe77c43348054f6ed150af10e
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06245742B1

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