Trifluoroacetic acid → (S)-N-((2S,3S)-5-((5-bromo-2-methoxynaphthalen-1-yl)methyl)-7-cyano-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide 2,2,2-trifluoroacetate

HRID 1486078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486078
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:49][CH3:50])=[C:7]2[CH2:12][N:13]1[C:19](=[O:20])[C@@H:18]([NH:21][C:22](=[O:34])[C@@H:23]([N:25](C)[C:26](=O)OC(C)(C)C)[CH3:24])[C@H:17]([CH3:35])[N:16]([C:36](=[O:42])[CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:15]2[CH:43]=[CH:44][C:45]([C:47]#[N:48])=[CH:46][C:14]1=2.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>C(Cl)Cl>[F:54][C:53]([F:56])([F:55])[C:51]([OH:57])=[O:52].[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:49][CH3:50])=[C:7]2[CH2:12][N:13]1[C:19](=[O:20])[C@@H:18]([NH:21][C:22](=[O:34])[C@@H:23]([NH:25][CH3:26])[CH3:24])[C@H:17]([CH3:35])[N:16]([C:36](=[O:42])[CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:15]2[CH:43]=[CH:44][C:45]([C:47]#[N:48])=[CH:46][C:14]1=2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 118292721tert-butyl(S)-1-((2S,3S)-5-((5-bromo-2-methoxynaphthalen-1-yl)methyl)-7-cyano-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Produkt 1

HCID 73425657(S)-N-((2S,3S)-5-((5-bromo-2-methoxynaphthalen-1-yl)methyl)-7-cyano-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide 2,2,2-trifluoroacetateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a rt solution of tert-butyl(S)-1-((2S,3S)-5-((5-bromo-2-methoxynaphthalen-1-yl)methyl)-7-cyano-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (68 mg, 88.2 μmol) in CH2Cl2 (353 μl) was added TFA (88.2 μl). The reaction was stirred at rt for 2.5 h, then concentrated, taken up in H2O, and lyophilized to provide (S)-N-((2S,3S)-5-((5-bromo-2-methoxynaphthalen-1-yl)methyl)-7-cyano-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide 2,2,2-trifluoroacetate (68.6 mg, 99%) as a white solid. MS m/z 670/672 (MH)+.

Aufarbeitung

  1. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7b302368bc81465b994265c16c506599
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422331B2

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