Triethylamine → Carbamate

HRID 1852121

Reaktionsgleichung

Reaktionsgleichung von HRID 1852121
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([NH:32][C@@H:33]([C@H:45]([CH3:53])[CH2:46][CH:47]([CH3:52])[CH2:48][CH2:49][CH:50]=[CH2:51])[C:34]([N:36]1[CH2:40][C@H:39]([OH:41])[CH2:38][C@H:37]1[C:42]([OH:44])=O)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26].Cl.[NH2:55][C@:56]1([C:61]([NH:63][S:64]([C:67]2([CH2:70][F:71])[CH2:69][CH2:68]2)(=[O:66])=[O:65])=[O:62])[CH2:58][C@H:57]1C=C.C(N(CC)CC)C>C(Cl)Cl>[F:71][CH2:70][C:67]1([S:64]([NH:63][C:61]([C@@:56]23[CH2:58][C@H:57]2[CH:51]=[CH:50][CH2:49][CH2:48][CH:47]([CH3:52])[CH2:46][C@@H:45]([CH3:53])[C@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:26])([CH3:28])[CH3:27])[C:34](=[O:35])[N:36]2[CH2:40][C@H:39]([OH:41])[CH2:38][C@H:37]2[C:42](=[O:44])[NH:55]3)=[O:62])(=[O:66])=[O:65])[CH2:68][CH2:69]1.[C:30](=[O:29])([O-:31])[NH2:32]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86683196(2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acidHCID 86683199HCID 86683199, Verbindung

Produkt 2

HCID 276CarbamateAusbeute 1.959,7 %HCID 71005415HCID 71005415, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

HATU (11.61 g, 30.5 mmol) was added to a solution of (2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid (10.50 g, 25.5 mmol), (1R,2S)-1-amino-N-((1-(fluoromethyl)cyclopropyl)sulfonyl)-2-vinylcyclopropanecarboxamide HCl (8.37 g, 28 mmol), and triethylamine (14.19 mL, 102 mmol) in DCM (220 mL) and was stirred at RT for overnight. The reaction was washed with 1N HCl (3×) and then brine and evaporated on rotovap. The crude material was purified by silica gel chromatography using 20-40% Acetone in hexanes. The product fractions were collected and the solvent removed under vacuum to give the desired product tert-butyl ((2S,3R)-1-((2S,4R)-2-(1R,2S)-1-(((1-(fluoromethyl)cyclopropyl)sulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate (15 g, 90% yield). MS: MS m/z 657.3 (M++1).

Aufarbeitung

  1. washThe reaction was washed with 1N HCl (3×)
  2. custombrine and evaporated on rotovap
  3. customThe crude material was purified by silica gel chromatography
  4. customThe product fractions were collected
  5. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3622bbc10ce544599b9a5b1645adc8d7
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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