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(2S)-2-(2-(((Benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetamido)-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide → (6S,9aS)-N-benzyl-8-((6-fluoropyridin-2-yl)methyl)-6-((4-hydroxyphenyl)methyl)-4,7-dioxo-2-(prop-2-en-1-yl)-octahydro-1H-pyrazino[2,1-c][1,2,4]triazine-1-carboxamide

HRID 707507
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 707507
[CH2:1]([NH:8][C:9]([NH:11][N:12]([CH2:49][CH:50]=[CH2:51])[CH2:13][C:14]([NH:16][C@@H:17]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44]C(C)(C)C)=[CH:40][CH:39]=1)[C:18]([N:20]([CH2:29][CH:30](OCC)OCC)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[N:23]=1)=[O:19])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)=O>[CH2:1]([NH:8][C:9]([N:11]1[C@H:30]2[CH2:29][N:20]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[N:23]=3)[C:18](=[O:19])[C@H:17]([CH2:37][C:38]3[CH:39]=[CH:40][C:41]([OH:44])=[CH:42][CH:43]=3)[N:16]2[C:14](=[O:15])[CH2:13][N:12]1[CH2:49][CH:50]=[CH2:51])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

3

Edukt 1

HCID 118162464(2S)-2-(2-(((Benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetamido)-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide

Produkt 1

HCID 118162437(6S,9aS)-N-benzyl-8-((6-fluoropyridin-2-yl)methyl)-6-((4-hydroxyphenyl)methyl)-4,7-dioxo-2-(prop-2-en-1-yl)-octahydro-1H-pyrazino[2,1-c][1,2,4]triazine-1-carboxamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixed solution of (2S)-2-(2-(((benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetamido)-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide (1.22 g, 1.73 mmol) described in Production Example 2-3 and formic acid (26 mL) was stirred at 70° C. for 3 hours. The reaction mixture was concentrated under a reduced pressure, water was added to the residue, and the resultant solution was extracted with ethyl acetate. An organic layer was washed with water and then with saturated brine, then dried over anhydrous magnesium sulfate, and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=20:1) to give the title compound (865 mg, yield: 90%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under a reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe resultant solution was extracted with ethyl acetate
  4. washAn organic layer was washed with water
  5. dry with materialwith saturated brine, then dried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under a reduced pressure
  8. customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-a6f42651eb534236b1bd2ee65e4118cf
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09174998B2

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