HCID 86612333, Verbindung → HCID 16226508, Verbindung

HRID 1517632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517632
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:27]([O:29][CH2:30][P:31]([O:41]CC1C=CC=CC=1)([O:33]CC1C=CC=CC=1)=[O:32])=[O:28])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2].CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][N:22]3[C:27]([O:29][CH2:30][P:31](=[O:32])([OH:41])[OH:33])=[O:28])=[O:16])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 86612333HCID 86612333, Verbindung

Produkt 1

HCID 16226508HCID 16226508, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

1.5 g (2.25 mmol) of the compound from Example 21C was added to a mixture of 0.3 g 20% Pd(OH)2/C and 150 mL methanol in a stainless steel autoclave. The reactor was sealed and flushed with nitrogen, and then it was pressurized with hydrogen (60 psi). The mixture was stirred at ambient temperature for 90 minutes. Product precipitated, added 150 mL tetrahydrofuran to redissolve, catalyst was filtered off, washed with methanol and tetrahydrofuran, and the filtrate was concentrated to provide 1.08 g (99%) of the title compound. MS (ESI) m/z: 485.21 [M−H]− 1H NMR (DMSO-d6) δ: 1.28 (s, 9H), 1.81-1.88 (m, 1H), 2.42-2.48 (m, 1H), 2.79-2.87 (m, 1H), 2.91-3.01 (m, 1H), 4.56 (d, 2H), 5.16 (q, 1H), 6.69 (d, 1H), 7.27 (s, 2H), 7.31 (s, 1H), 7.50 (t, 1H), 7.72 (d, 1H), 7.89 (d, 1H), 8.43 (s, 1H), 8.85 (s, 1H).

Aufarbeitung

  1. customThe reactor was sealed
  2. customflushed with nitrogen
  3. customProduct precipitated
  4. additionadded 150 mL tetrahydrofuran
  5. dissolutionto redissolve
  6. filtrationcatalyst was filtered off
  7. washwashed with methanol and tetrahydrofuran
  8. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-baa4cfd95deb4324b8ed777b092b1fb5
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232309B2

Notizen zur Reaktion

Wird geladen…