(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate → HCID 88578517, Verbindung

HRID 1771248

Reaktionsgleichung

Reaktionsgleichung von HRID 1771248
[P:1]([O:13][CH2:14][O:15][C@@H:16]([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=1[C:72]1[CH:77]=[CH:76][C:75]([Cl:78])=[CH:74][CH:73]=1)[CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:65])[NH:30][S:31]([C:34]3[CH:39]=[CH:38][C:37]([NH:40][C@H:41]([CH2:50][CH2:51][N:52]4[CH2:57][CH2:56][O:55][CH2:54][CH2:53]4)[CH2:42][S:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[C:36]([S:58]([C:61]([F:64])([F:63])[F:62])(=[O:60])=[O:59])[CH:35]=3)(=[O:33])=[O:32])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)([O:8]C(C)(C)C)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O=C1[C@H](NC(=O)OCC2C=CC=CC=2)CC(=O)O1>CC(C)=O>[P:1]([OH:8])([O:13][CH2:14][O:15][C@@H:16]([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=1[C:72]1[CH:77]=[CH:76][C:75]([Cl:78])=[CH:74][CH:73]=1)[CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:24]=[CH:25][C:26]([C:29](=[O:65])[NH:30][S:31]([C:34]3[CH:39]=[CH:38][C:37]([NH:40][C@H:41]([CH2:50][CH2:51][N:52]4[CH2:53][CH2:54][O:55][CH2:56][CH2:57]4)[CH2:42][S:43][C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)=[C:36]([S:58]([C:61]([F:63])([F:62])[F:64])(=[O:59])=[O:60])[CH:35]=3)(=[O:32])=[O:33])=[CH:27][CH:28]=2)[CH2:19][CH2:18]1)([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Komponenten

4

Edukt 2

HCID 12416472(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamateHCID 131734652Di-tert-butyl ((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)-phenyl)piperidin-4-yl)methoxy)methyl phosphate

Produkt 1

HCID 88578517HCID 88578517, VerbindungAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Nitrolotrimethanol (5.27 mg, 0.05 mmol) was added to a solution of di-tert-butyl ((R)-(4′-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methoxy)methyl phosphate (EXAMPLE 27, 58.0 mg, 0.05 mmol) in acetone (1.8 ml) and 0.6 ml of pH7.2 buffer (Gibco, Dulbecco's Phosphate Buffered saline 1×). The resulting reaction mixture was stirred at 65° C. for 16 hours. Evaporation of the volatiles under reduced pressure gave a residue which was purified by reverse phase HPLC (Gilson column, eluting with 30→50% H2O with 10 mM NH4OAc/MeCN for 5 minutes) to provide the title product (0.017 g, yield: 19%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customEvaporation of the volatiles under reduced pressure
  3. customgave a residue which
  4. customwas purified by reverse phase HPLC (Gilson column, eluting with 30→50% H2O with 10 mM NH4OAc/MeCN for 5 minutes)

Quellen und Nachweise

ORD-Eintrag
ord-97612f8274f046aca759c27574b72d83
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09248140B2

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