(S)-benzyl 4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoate → (S)-4-Methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoic acid

HRID 630633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 630633
[CH3:1][CH:2]([CH3:45])[CH2:3][C@H:4]([N:15]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C:16](=[O:36])[C@@H:17]([NH:26][C:27](=[O:35])[CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6]>CO.O.CO.[Pd]>[CH3:1][CH:2]([CH3:45])[CH2:3][C@H:4]([N:15]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[C:16](=[O:36])[C@@H:17]([NH:26][C:27](=[O:35])[CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 1

HCID 86715394(S)-benzyl 4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoate

Produkt 1

HCID 86715393(S)-4-Methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoic acidAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

Referring to FIG. 45, a slurry of Pd/C (10%) (200 mg) in MeOH/water (9:1) (10 mL) was added to a solution of (S)-benzyl 4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenyl-N-((pivaloyloxy)methyl)butanamido)pentanoate (440 mg, 0.7 mmol) in MeOH (100 mL) and the suspension was stirred overnight under an atmosphere of hydrogen at RT. The reaction mixture was filtered over Celite, washed with MeOH and concentrated in vacuo to yield product (345 mg, 92%) as a colorless oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over Celite
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1fac1aff7a604d078446edb4f6adc527
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315542B2

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