(S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid benzyl ester → HCID 86709693, Verbindung

HRID 61290

Reaktionsgleichung

Reaktionsgleichung von HRID 61290
C([O:8][C:9](=[O:24])[C@@H:10]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][O:12][CH:13]([F:15])[F:14])C1C=CC=CC=1>C1COCC1.[Pd]>[C:20]([O:19][C:17]([NH:16][C@@H:10]([CH2:11][O:12][CH:13]([F:14])[F:15])[C:9]([OH:24])=[O:8])=[O:18])([CH3:23])([CH3:21])[CH3:22]

Komponenten

4

Edukt 1

HCID 90041473(S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid benzyl ester

Produkt 1

HCID 86709693HCID 86709693, VerbindungAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the compound of Formula XIII(a), (S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid benzyl ester (1.76 g, 5.09 mmol) in THF was stirred with 10% Pd/C (360 mg) under a hydrogen atmosphere for 2 hours. The reaction mixture was filtered and concentrated to give the compound of Formula IV(a), (S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid (1.3 g, 100%) as a sticky, colorless oil. 1H NMR (300 MHz, CDCl3): δ (ppm) 6.21 (wt, 1H), 5.35 (d, 1H), 4.59 (m, 1H), 4.35 (m, 1H), 4.21 (m, 1H) and 1.42 (s, 9H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7594e7f9c27343a4a2c736838633cf8d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441012B2

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