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Water → HCID 25125062, Verbindung

HRID 2038575
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2038575
C1([N:6]([C@@H:10]([C:44]([CH3:47])([CH3:46])[CH3:45])[C:11]([N:13]2[C@H:17]([C:18](=[O:32])[NH:19][CH:20]([CH2:29][CH2:30][CH3:31])[C@H:21]([OH:28])[C:22]([NH:24][CH:25]3[CH2:27][CH2:26]3)=[O:23])[CH2:16][C@@:15]3([CH2:36][C:35](=[O:37])[N:34]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH2:33]3)[CH2:14]2)=[O:12])[C:7](=O)[O-:8])CCCC1.O[NH-].CC(OI1(OC(C)=O)(OC(C)=O)O[C:61](=O)[C:60]2[CH:59]=[CH:58][CH:57]=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH2:79]>C(Cl)Cl>[CH:57]1([O:79][C:7](=[O:8])[NH:6][C@@H:10]([C:44]([CH3:47])([CH3:46])[CH3:45])[C:11]([N:13]2[C@H:17]([C:18](=[O:32])[NH:19][C@@H:20]([CH2:29][CH2:30][CH3:31])[C:21](=[O:28])[C:22]([NH:24][CH:25]3[CH2:27][CH2:26]3)=[O:23])[CH2:16][C@@:15]3([CH2:36][C:35](=[O:37])[N:34]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH2:33]3)[CH2:14]2)=[O:12])[CH2:58][CH2:59][CH2:60][CH2:61]1
KomponentenVersuchsvorschriftQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 178449504HCID 178449504, Verbindung

Produkt 1

HCID 25125062HCID 25125062, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

The hydroxy amide cyclopentyl-(S)-1-((3S,5R)-3-((S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)-8-oxo-7-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (J6a) (4.1 mg, 6.3 μmol) was dissolved in CH2Cl2 (1.0 ml) and treated with Dess-Martin periodinane (DMP, 8.0 mg, 18.9 μmol, 3 eq) for 3 hrs at room temp. The reaction was quenched with 1M sodium thiosulfate in water (32 μl, 5 eq). The reaction was loaded onto silica (eluted with ethyl acetate/hexane gradient) to give cyclopentyl-(S)-1-((3S,5R)-3-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-ylcarbamoyl)-8-oxo-7-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (compound no. 1) (3.1 mg, 4.8 μmol) as a white solid. NMR (CDCl3) δ5195m, 46H), 1.96 (m, 1H), 2.25 (m, 1H), 2.61 (m, 2H), 2.80 (s, 2H), 3.60 (dd, 2H), 4.00 (d, 1H), 4.22 (m, 2H), 4.70 (m, 1H), 4.90 (m, 1H), 5.20 (d, 1H), 5.35 (m, 1H), 6.90 (s, 1H), 7.19 (m, 1H), 7.38 (m, 2H), 7.65 (d, 1H). LCMS for C35H49N5O7 651.36 [M], found ES+ 652.5 [M+H]+ and ES− 650.6 [M−H]−, at 3.2 minutes retention time, using 10-90% acetonitrile/water (with 0.1% formic acid buffer) gradient over 5 minutes. The minor diastereomer cyclopentyl (S)-1-((3S,5S)-3-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-ylcarbamoyl)-8-oxo-7-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (compound no. 4) (1.4 mg, 2 pimp was obtained in similar fashion. 1H NMR (CDCl3) δ0.52 (m, 2H), 71m, 14H), 1.0-2.0 (m, 22H), 2.10 (m, 1H), 2.45-2.75 (m, 4H), 3.64 (t, 2H), 3.90 (d, 2H), 4.15 (d, 1H), 4.60 (m, 1H), 5.00 (m, 1H), 5.13 (d, 1H), 5.25 (m, 1H), 6.80 (m, 1H), 7.10 (m, 2H), 7.30 (m, 4H), 7.50 (m, 2H), 7.90 (m, 1H); LCMS for C35H49N5O7 651.36 [M], found ES+652.5 [M+H]+ and ES− 650.6 [M−H]−, at 3.2 minutes retention time, using 10-90% acetonitrile/water (with 0.1% formic acid buffer) gradient over 5 minutes.

Quellen und Nachweise

ORD-Eintrag
ord-522139d2077c48ecb0d3cb84f670eaac
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08575208B2

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